diff --git a/.github/workflows/rubocop.yml b/.github/workflows/rubocop.yml
index fdefa3c5..de8995ca 100644
--- a/.github/workflows/rubocop.yml
+++ b/.github/workflows/rubocop.yml
@@ -16,10 +16,9 @@ jobs:
       - uses: actions/checkout@v2
       - uses: ruby/setup-ruby@v1
         with:
-          ruby-version: 2.5.8 # Not needed with a .ruby-version file
+          ruby-version: 3.3.0
           bundler-cache: true # runs 'bundle install' and caches installed gems automatically
 
       - run: |
-          gem install bundler --version 1.17.3 -N
-          bundle _1.17.3_ install -j 12
+          bundle install -j 12
           bundle exec rubocop --format progress -P
diff --git a/.github/workflows/ruby.yml b/.github/workflows/ruby.yml
index feb3fdab..57958291 100644
--- a/.github/workflows/ruby.yml
+++ b/.github/workflows/ruby.yml
@@ -11,7 +11,7 @@ jobs:
     runs-on: ubuntu-latest
     services:
       postgres:
-        image: postgres:13
+        image: postgres:15
         ports:
           - 5432:5432
         env:
@@ -27,13 +27,12 @@ jobs:
       - uses: actions/checkout@v2
       - uses: ruby/setup-ruby@v1
         with:
-          ruby-version: 2.5.8 # Not needed with a .ruby-version file
+          ruby-version: 3.3.0
           bundler-cache: true # runs 'bundle install' and caches installed gems automatically
 
       - run: |
-          gem update --system 3.2.3 || true
-          gem install bundler --version 1.17.3 -N
-          bundle _1.17.3_ install -j 12
+          gem update --system || true
+          install -j 12
 
       - run: |
           bundle exec rake db:create
@@ -41,4 +40,4 @@ jobs:
           bundle exec rake db:test:prepare
 
       - run: |
-          bundle exec rspec 
+          bundle exec rspec  -b
diff --git a/.rubocop_todo.yml b/.rubocop_todo.yml
index ceaf9ed4..75bff208 100644
--- a/.rubocop_todo.yml
+++ b/.rubocop_todo.yml
@@ -1,17 +1,17 @@
 # This configuration was generated by
 # `rubocop --auto-gen-config`
-# on 2022-05-02 03:13:36 UTC using RuboCop version 1.27.0.
+# on 2024-02-16 22:39:17 UTC using RuboCop version 1.60.2.
 # The point is for the user to remove these configuration records
 # one by one as the offenses are removed from the code base.
 # Note that changes in the inspected code, or installation of new
 # versions of RuboCop, may require this file to be generated again.
 
-# Offense count: 2
+# Offense count: 1
+# This cop supports unsafe autocorrection (--autocorrect-all).
 # Configuration parameters: AllowSafeAssignment.
 Lint/AssignmentInCondition:
   Exclude:
     - 'app/controllers/passwords_controller.rb'
-    - 'app/controllers/ticket_requests_controller.rb'
 
 # Offense count: 1
 Lint/ShadowingOuterLocalVariable:
@@ -24,61 +24,247 @@ Lint/UnmodifiedReduceAccumulator:
     - 'app/helpers/shifts_helper.rb'
 
 # Offense count: 1
+# This cop supports unsafe autocorrection (--autocorrect-all).
 Lint/UselessAssignment:
   Exclude:
     - 'config/unicorn.rb'
 
-# Offense count: 20
-# Configuration parameters: IgnoredMethods, CountRepeatedAttributes.
+# Offense count: 19
+# Configuration parameters: AllowedMethods, AllowedPatterns, CountRepeatedAttributes.
 Metrics/AbcSize:
   Max: 62
 
-# Offense count: 21
-# Configuration parameters: CountComments, CountAsOne, ExcludedMethods, IgnoredMethods.
-# IgnoredMethods: refine
+# Offense count: 3
+# Configuration parameters: CountComments, CountAsOne, AllowedMethods, AllowedPatterns, inherit_mode.
+# AllowedMethods: refine
 Metrics/BlockLength:
-  Max: 255
+  Max: 55
 
-# Offense count: 2
+# Offense count: 3
 # Configuration parameters: CountComments, CountAsOne.
 Metrics/ClassLength:
-  Max: 157
+  Max: 156
 
-# Offense count: 4
-# Configuration parameters: IgnoredMethods.
+# Offense count: 5
+# Configuration parameters: AllowedMethods, AllowedPatterns.
 Metrics/CyclomaticComplexity:
   Max: 13
 
-# Offense count: 25
-# Configuration parameters: CountComments, CountAsOne, ExcludedMethods, IgnoredMethods.
+# Offense count: 24
+# Configuration parameters: CountComments, CountAsOne, AllowedMethods, AllowedPatterns.
 Metrics/MethodLength:
-  Max: 59
+  Max: 58
 
 # Offense count: 1
 # Configuration parameters: CountComments, CountAsOne.
 Metrics/ModuleLength:
   Max: 114
 
-# Offense count: 3
-# Configuration parameters: IgnoredMethods.
+# Offense count: 4
+# Configuration parameters: AllowedMethods, AllowedPatterns.
 Metrics/PerceivedComplexity:
   Max: 15
 
 # Offense count: 6
 # Configuration parameters: MinNameLength, AllowNamesEndingInNumbers, AllowedNames, ForbiddenNames.
-# AllowedNames: at, by, db, id, in, io, ip, of, on, os, pp, to
+# AllowedNames: as, at, by, cc, db, id, if, in, io, ip, of, on, os, pp, to
 Naming/MethodParameterName:
   Exclude:
     - 'spec/support/factory_bot.rb'
     - 'spec/support/time_extensions.rb'
 
-# Offense count: 74
+# Offense count: 15
+# Configuration parameters: Prefixes, AllowedPatterns.
+# Prefixes: when, with, without
+RSpec/ContextWording:
+  Exclude:
+    - 'spec/controllers/events_controller_spec.rb'
+    - 'spec/models/event_spec.rb'
+    - 'spec/models/ticket_request_spec.rb'
+
+# Offense count: 1
+# Configuration parameters: IgnoredMetadata.
+RSpec/DescribeClass:
+  Exclude:
+    - 'spec/lib/fnf/music_submissions_spec.rb'
+
+# Offense count: 1
+RSpec/ExpectInHook:
+  Exclude:
+    - 'spec/lib/fnf/event_reporter_spec.rb'
+
+# Offense count: 1
+# Configuration parameters: .
+# SupportedStyles: have_received, receive
+RSpec/MessageSpies:
+  EnforcedStyle: receive
+
+# Offense count: 15
+# Configuration parameters: AllowSubject.
+RSpec/MultipleMemoizedHelpers:
+  Max: 11
+
+# Offense count: 3
+# Configuration parameters: EnforcedStyle, IgnoreSharedExamples.
+# SupportedStyles: always, named_only
+RSpec/NamedSubject:
+  Exclude:
+    - 'spec/controllers/ticket_requests_controller_spec.rb'
+    - 'spec/lib/fnf/csv_reader_spec.rb'
+    - 'spec/models/ticket_request_spec.rb'
+
+# Offense count: 60
+# Configuration parameters: AllowedGroups.
+RSpec/NestedGroups:
+  Max: 5
+
+# Offense count: 52
+# Configuration parameters: AllowedPatterns.
+# AllowedPatterns: ^expect_, ^assert_
+RSpec/NoExpectationExample:
+  Exclude:
+    - 'spec/controllers/emails_controller_spec.rb'
+    - 'spec/controllers/events_controller_spec.rb'
+    - 'spec/controllers/ticket_requests_controller_spec.rb'
+    - 'spec/lib/fnf/event_reporter_spec.rb'
+    - 'spec/mailers/payment_mailer_spec.rb'
+    - 'spec/mailers/ticket_request_mailer_spec.rb'
+    - 'spec/models/event_spec.rb'
+    - 'spec/models/ticket_request_spec.rb'
+    - 'spec/models/user_spec.rb'
+
+# Offense count: 2
+RSpec/RepeatedExampleGroupBody:
+  Exclude:
+    - 'spec/models/event_spec.rb'
+
+# Offense count: 3
+# This cop supports unsafe autocorrection (--autocorrect-all).
+Rails/ApplicationMailer:
+  Exclude:
+    - 'app/mailers/eald_payment_mailer.rb'
+    - 'app/mailers/payment_mailer.rb'
+    - 'app/mailers/ticket_request_mailer.rb'
+
+# Offense count: 9
+# Configuration parameters: Database, Include.
+# SupportedDatabases: mysql, postgresql
+# Include: db/**/*.rb
+Rails/BulkChangeTable:
+  Exclude:
+    - 'db/migrate/20130226221916_add_user_to_ticket_request.rb'
+    - 'db/migrate/20130325024448_add_ticket_cost_info_to_event.rb'
+    - 'db/migrate/20130803212458_add_start_and_end_ticket_sale_times_to_events.rb'
+    - 'db/migrate/20140428045329_add_role_to_ticket_requests.rb'
+    - 'db/migrate/20140605045004_extract_address_into_multiple_fields.rb'
+    - 'db/migrate/20140616030905_change_camping_type_on_ticket_requests.rb'
+    - 'db/migrate/20160611234315_add_eald_columns.rb'
+
+# Offense count: 3
+# Configuration parameters: Include.
+# Include: app/models/**/*.rb
+Rails/HasManyOrHasOneDependent:
+  Exclude:
+    - 'app/models/event.rb'
+    - 'app/models/ticket_request.rb'
+    - 'app/models/user.rb'
+
+# Offense count: 3
+# Configuration parameters: Include.
+# Include: app/helpers/**/*.rb
+Rails/HelperInstanceVariable:
+  Exclude:
+    - 'app/helpers/shifts_helper.rb'
+
+# Offense count: 14
+Rails/I18nLocaleTexts:
+  Exclude:
+    - 'app/controllers/home_controller.rb'
+    - 'app/controllers/jobs_controller.rb'
+    - 'app/controllers/passwords_controller.rb'
+    - 'app/controllers/payments_controller.rb'
+    - 'app/controllers/shifts_controller.rb'
+    - 'app/controllers/ticket_requests_controller.rb'
+    - 'app/models/event_admin.rb'
+    - 'app/models/payment.rb'
+    - 'app/models/site_admin.rb'
+    - 'app/models/user.rb'
+
+# Offense count: 1
+# Configuration parameters: Database, Include.
+# SupportedDatabases: mysql
+# Include: db/**/*.rb
+Rails/NotNullColumn:
+  Exclude:
+    - 'db/migrate/20130311213508_add_event_id_to_ticket_request.rb'
+
+# Offense count: 9
+# Configuration parameters: Include.
+# Include: db/**/*.rb
+Rails/ReversibleMigration:
+  Exclude:
+    - 'db/migrate/20130226221916_add_user_to_ticket_request.rb'
+    - 'db/migrate/20140515053804_remove_performer_from_ticket_requests.rb'
+    - 'db/migrate/20140605045004_extract_address_into_multiple_fields.rb'
+    - 'db/migrate/20140605052627_remove_volunteer_shifts_from_ticket_requests.rb'
+    - 'db/migrate/20140605053705_remove_ask_how_many_shifts_from_events.rb'
+    - 'db/migrate/20140605060026_add_camping_type_to_ticket_requests.rb'
+    - 'db/migrate/20140616030905_change_camping_type_on_ticket_requests.rb'
+
+# Offense count: 3
+# Configuration parameters: ForbiddenMethods, AllowedMethods.
+# ForbiddenMethods: decrement!, decrement_counter, increment!, increment_counter, insert, insert!, insert_all, insert_all!, toggle!, touch, touch_all, update_all, update_attribute, update_column, update_columns, update_counters, upsert, upsert_all
+Rails/SkipsModelValidations:
+  Exclude:
+    - 'app/controllers/application_controller.rb'
+    - 'app/controllers/ticket_requests_controller.rb'
+    - 'app/models/user.rb'
+
+# Offense count: 3
+# Configuration parameters: Include.
+# Include: db/**/*.rb
+Rails/ThreeStateBooleanColumn:
+  Exclude:
+    - 'db/migrate/20140515054433_add_vehicle_camping_requested_to_ticket_requests.rb'
+    - 'db/migrate/20140616030905_change_camping_type_on_ticket_requests.rb'
+    - 'db/migrate/20150609064608_add_agrees_terms_to_ticket_requests.rb'
+
+# Offense count: 1
+# Configuration parameters: TransactionMethods.
+Rails/TransactionExitStatement:
+  Exclude:
+    - 'app/models/ticket_request.rb'
+
+# Offense count: 2
+# Configuration parameters: Include.
+# Include: app/models/**/*.rb
+Rails/UniqueValidationWithoutIndex:
+  Exclude:
+    - 'app/models/payment.rb'
+    - 'app/models/site_admin.rb'
+
+# Offense count: 2
+# This cop supports safe autocorrection (--autocorrect).
+Rake/Desc:
+  Exclude:
+    - 'Rakefile'
+
+# Offense count: 81
 # Configuration parameters: AllowedConstants.
 Style/Documentation:
   Enabled: false
 
+# Offense count: 1
+# This cop supports unsafe autocorrection (--autocorrect-all).
+# Configuration parameters: EnforcedStyle.
+# SupportedStyles: always, always_true, never
+Style/FrozenStringLiteralComment:
+  Exclude:
+    - 'app/models/application_record.rb'
+
 # Offense count: 5
-# Configuration parameters: MinBodyLength.
+# This cop supports safe autocorrection (--autocorrect).
+# Configuration parameters: MinBodyLength, AllowConsecutiveConditionals.
 Style/GuardClause:
   Exclude:
     - 'app/controllers/application_controller.rb'
@@ -92,9 +278,9 @@ Style/MissingRespondToMissing:
   Exclude:
     - 'spec/support/factory_bot.rb'
 
-# Offense count: 3
-# This cop supports safe auto-correction (--auto-correct).
-# Configuration parameters: AllowHeredoc, AllowURI, URISchemes, IgnoreCopDirectives, IgnoredPatterns.
+# Offense count: 7
+# This cop supports safe autocorrection (--autocorrect).
+# Configuration parameters: AllowHeredoc, AllowURI, URISchemes, IgnoreCopDirectives, AllowedPatterns.
 # URISchemes: http, https
 Layout/LineLength:
   Max: 174
diff --git a/.ruby-version b/.ruby-version
index be94e6f5..15a27998 100644
--- a/.ruby-version
+++ b/.ruby-version
@@ -1 +1 @@
-3.2.2
+3.3.0
diff --git a/Brewfile b/Brewfile
index a45af24a..cf525934 100644
--- a/Brewfile
+++ b/Brewfile
@@ -56,6 +56,7 @@ brew 'rsync'
 brew 'ruby-build'
 brew 'ruby-completion'
 brew 'shellcheck'
+brew 'stripe/stripe-mock/stripe-mock'
 brew 'tree'
 brew 'vim'
 brew 'watch'
diff --git a/Brewfile.lock.json b/Brewfile.lock.json
index 248fb8c7..ede91c28 100644
--- a/Brewfile.lock.json
+++ b/Brewfile.lock.json
@@ -939,60 +939,45 @@
         }
       },
       "libffi": {
-        "version": "3.4.4",
+        "version": "3.4.5",
         "bottle": {
           "rebuild": 0,
           "root_url": "https://ghcr.io/v2/homebrew/core",
           "files": {
             "arm64_sonoma": {
               "cellar": ":any",
-              "url": "https://ghcr.io/v2/homebrew/core/libffi/blobs/sha256:35b8d6504f17f98eba5b432a0bf33936d7ca0c5ab1983cefba128621210f69ef",
-              "sha256": "35b8d6504f17f98eba5b432a0bf33936d7ca0c5ab1983cefba128621210f69ef"
+              "url": "https://ghcr.io/v2/homebrew/core/libffi/blobs/sha256:05b449dea2ce5e3f9d0a68557ab04938dc95c179bd33797e8b455efab7861241",
+              "sha256": "05b449dea2ce5e3f9d0a68557ab04938dc95c179bd33797e8b455efab7861241"
             },
             "arm64_ventura": {
               "cellar": ":any",
-              "url": "https://ghcr.io/v2/homebrew/core/libffi/blobs/sha256:66d9dcb218283c43250b04e507b7b96f0cf18fb1017fcaf811729324d11127f7",
-              "sha256": "66d9dcb218283c43250b04e507b7b96f0cf18fb1017fcaf811729324d11127f7"
+              "url": "https://ghcr.io/v2/homebrew/core/libffi/blobs/sha256:c1f444ded62e9fc4da1179f2f1f18bbf3db6be8d8e3b764f52d3370a6a534ed3",
+              "sha256": "c1f444ded62e9fc4da1179f2f1f18bbf3db6be8d8e3b764f52d3370a6a534ed3"
             },
             "arm64_monterey": {
               "cellar": ":any",
-              "url": "https://ghcr.io/v2/homebrew/core/libffi/blobs/sha256:e7ea0921a053dc81e818c3893887e819ed26c0e231fd306e05e905b51b9ea902",
-              "sha256": "e7ea0921a053dc81e818c3893887e819ed26c0e231fd306e05e905b51b9ea902"
-            },
-            "arm64_big_sur": {
-              "cellar": ":any",
-              "url": "https://ghcr.io/v2/homebrew/core/libffi/blobs/sha256:8d44b24963c114512934de23cc776a6190f5bcb65db8e6cc65e1b60122571747",
-              "sha256": "8d44b24963c114512934de23cc776a6190f5bcb65db8e6cc65e1b60122571747"
+              "url": "https://ghcr.io/v2/homebrew/core/libffi/blobs/sha256:971cbcb1d220e448683bbc76c561e03e41610a8ce4065b9be92e2e7e838c4a07",
+              "sha256": "971cbcb1d220e448683bbc76c561e03e41610a8ce4065b9be92e2e7e838c4a07"
             },
             "sonoma": {
               "cellar": ":any",
-              "url": "https://ghcr.io/v2/homebrew/core/libffi/blobs/sha256:8d52eea700d32139fb1844e58af00397bf9fe0bbe297bcc9c0b7a2a769725419",
-              "sha256": "8d52eea700d32139fb1844e58af00397bf9fe0bbe297bcc9c0b7a2a769725419"
+              "url": "https://ghcr.io/v2/homebrew/core/libffi/blobs/sha256:70c125b86120c56b00f737b46f207da0b46d54233367d36d53ea774562e39c18",
+              "sha256": "70c125b86120c56b00f737b46f207da0b46d54233367d36d53ea774562e39c18"
             },
             "ventura": {
               "cellar": ":any",
-              "url": "https://ghcr.io/v2/homebrew/core/libffi/blobs/sha256:a86ed7eb1b02a3d44cd6e75977c910466357a1715743f89be94416d000577133",
-              "sha256": "a86ed7eb1b02a3d44cd6e75977c910466357a1715743f89be94416d000577133"
+              "url": "https://ghcr.io/v2/homebrew/core/libffi/blobs/sha256:4aff209ef6d0aadd8dbc6384deb2cb1173bed527e27838142ab2c5b93a647e76",
+              "sha256": "4aff209ef6d0aadd8dbc6384deb2cb1173bed527e27838142ab2c5b93a647e76"
             },
             "monterey": {
               "cellar": ":any",
-              "url": "https://ghcr.io/v2/homebrew/core/libffi/blobs/sha256:9dd80c4c3d4451cc3216dbf1129a2bddec474aa9266b6bb5c603e0a6cce7605b",
-              "sha256": "9dd80c4c3d4451cc3216dbf1129a2bddec474aa9266b6bb5c603e0a6cce7605b"
-            },
-            "big_sur": {
-              "cellar": ":any",
-              "url": "https://ghcr.io/v2/homebrew/core/libffi/blobs/sha256:b5c4e2054802f97a68b8f32d9ff2c6782f9a37223cd0a3b3d2175ecf04740a4f",
-              "sha256": "b5c4e2054802f97a68b8f32d9ff2c6782f9a37223cd0a3b3d2175ecf04740a4f"
-            },
-            "catalina": {
-              "cellar": ":any",
-              "url": "https://ghcr.io/v2/homebrew/core/libffi/blobs/sha256:1f53646211da139b423eb38f923bc38da1de86b7a68bfc2df5351098fe3c67e3",
-              "sha256": "1f53646211da139b423eb38f923bc38da1de86b7a68bfc2df5351098fe3c67e3"
+              "url": "https://ghcr.io/v2/homebrew/core/libffi/blobs/sha256:7c96a49210ba55ce4473d36c2dbd86192ae33f2c267ee47b5ed0e970aea62093",
+              "sha256": "7c96a49210ba55ce4473d36c2dbd86192ae33f2c267ee47b5ed0e970aea62093"
             },
             "x86_64_linux": {
               "cellar": ":any_skip_relocation",
-              "url": "https://ghcr.io/v2/homebrew/core/libffi/blobs/sha256:dcc9412995b5e319f64796a77b1eb8e684f1d1b6b5d7ac824f434ada692e4ff8",
-              "sha256": "dcc9412995b5e319f64796a77b1eb8e684f1d1b6b5d7ac824f434ada692e4ff8"
+              "url": "https://ghcr.io/v2/homebrew/core/libffi/blobs/sha256:ad76b74572cf5792f5160938bd6ae8b934f0d021abd300d45feba51dca1313fc",
+              "sha256": "ad76b74572cf5792f5160938bd6ae8b934f0d021abd300d45feba51dca1313fc"
             }
           }
         }
@@ -2443,45 +2428,45 @@
         }
       },
       "yamllint": {
-        "version": "1.34.0",
+        "version": "1.35.1",
         "bottle": {
           "rebuild": 0,
           "root_url": "https://ghcr.io/v2/homebrew/core",
           "files": {
             "arm64_sonoma": {
               "cellar": ":any_skip_relocation",
-              "url": "https://ghcr.io/v2/homebrew/core/yamllint/blobs/sha256:e2c7af04cad22bf7774b178d359194640840e0120b085f1ff9357dbfeb869c52",
-              "sha256": "e2c7af04cad22bf7774b178d359194640840e0120b085f1ff9357dbfeb869c52"
+              "url": "https://ghcr.io/v2/homebrew/core/yamllint/blobs/sha256:16120f61c559ec5fd83bb28d110b265d7bfeb38fb5f6ae3958b6edddc3836fde",
+              "sha256": "16120f61c559ec5fd83bb28d110b265d7bfeb38fb5f6ae3958b6edddc3836fde"
             },
             "arm64_ventura": {
               "cellar": ":any_skip_relocation",
-              "url": "https://ghcr.io/v2/homebrew/core/yamllint/blobs/sha256:d3fa38fc60cb71ac91560aea632134c104520e0f01a06abbd20364211ae1a989",
-              "sha256": "d3fa38fc60cb71ac91560aea632134c104520e0f01a06abbd20364211ae1a989"
+              "url": "https://ghcr.io/v2/homebrew/core/yamllint/blobs/sha256:9ede8ae30ddc0615758e87836e91d84e712616801d17c0ff0ae1ebb737f4ae7f",
+              "sha256": "9ede8ae30ddc0615758e87836e91d84e712616801d17c0ff0ae1ebb737f4ae7f"
             },
             "arm64_monterey": {
               "cellar": ":any_skip_relocation",
-              "url": "https://ghcr.io/v2/homebrew/core/yamllint/blobs/sha256:accbbf0eb1134eeceb373cc9bb09052c3a1f28806aa89de212b95ab5c24e6ea9",
-              "sha256": "accbbf0eb1134eeceb373cc9bb09052c3a1f28806aa89de212b95ab5c24e6ea9"
+              "url": "https://ghcr.io/v2/homebrew/core/yamllint/blobs/sha256:ee60920ab2ac09300844b9a0ddadef8b212d331e77ad00a3a8d163ce4651860a",
+              "sha256": "ee60920ab2ac09300844b9a0ddadef8b212d331e77ad00a3a8d163ce4651860a"
             },
             "sonoma": {
               "cellar": ":any_skip_relocation",
-              "url": "https://ghcr.io/v2/homebrew/core/yamllint/blobs/sha256:6caee252f7d4768297704a7378f517d53608352aef512fa6da8b0dddd43d20a6",
-              "sha256": "6caee252f7d4768297704a7378f517d53608352aef512fa6da8b0dddd43d20a6"
+              "url": "https://ghcr.io/v2/homebrew/core/yamllint/blobs/sha256:3a9a0bfa4caf102c09649e2c5ef5d8c33da13ffc0390c167ed6b4b35b8715b5f",
+              "sha256": "3a9a0bfa4caf102c09649e2c5ef5d8c33da13ffc0390c167ed6b4b35b8715b5f"
             },
             "ventura": {
               "cellar": ":any_skip_relocation",
-              "url": "https://ghcr.io/v2/homebrew/core/yamllint/blobs/sha256:dbbe3c4287f505126715bbf5f36dc98b22d6a6136724fc95f9154fa1578c877a",
-              "sha256": "dbbe3c4287f505126715bbf5f36dc98b22d6a6136724fc95f9154fa1578c877a"
+              "url": "https://ghcr.io/v2/homebrew/core/yamllint/blobs/sha256:8d1074f726fc3dce640a3c19542edcac8bfd67676508c43879ed833d919a12b1",
+              "sha256": "8d1074f726fc3dce640a3c19542edcac8bfd67676508c43879ed833d919a12b1"
             },
             "monterey": {
               "cellar": ":any_skip_relocation",
-              "url": "https://ghcr.io/v2/homebrew/core/yamllint/blobs/sha256:6416777b4fc9e8f1e1ebabc9284778918554ad8792f894b322d10ad57ca7acb6",
-              "sha256": "6416777b4fc9e8f1e1ebabc9284778918554ad8792f894b322d10ad57ca7acb6"
+              "url": "https://ghcr.io/v2/homebrew/core/yamllint/blobs/sha256:9c609546ff7edd2d308ec5dc3e49676eeab8eda9ef9211571aadeeeeee74920b",
+              "sha256": "9c609546ff7edd2d308ec5dc3e49676eeab8eda9ef9211571aadeeeeee74920b"
             },
             "x86_64_linux": {
               "cellar": ":any_skip_relocation",
-              "url": "https://ghcr.io/v2/homebrew/core/yamllint/blobs/sha256:b1fe6d3f1bf98b489c8d89000d0f69c091ee5d76c3ec46d09d375628368d1a00",
-              "sha256": "b1fe6d3f1bf98b489c8d89000d0f69c091ee5d76c3ec46d09d375628368d1a00"
+              "url": "https://ghcr.io/v2/homebrew/core/yamllint/blobs/sha256:8799f333c63d658c4dd6d87113fab523b23b8e41940e869c50e4205609145bb7",
+              "sha256": "8799f333c63d658c4dd6d87113fab523b23b8e41940e869c50e4205609145bb7"
             }
           }
         }
@@ -2531,45 +2516,45 @@
         }
       },
       "yq": {
-        "version": "4.40.7",
+        "version": "4.41.1",
         "bottle": {
           "rebuild": 0,
           "root_url": "https://ghcr.io/v2/homebrew/core",
           "files": {
             "arm64_sonoma": {
               "cellar": ":any_skip_relocation",
-              "url": "https://ghcr.io/v2/homebrew/core/yq/blobs/sha256:ae120bb652a1899b07742773b3f29d092252466e758e11b9936b8adb758ac098",
-              "sha256": "ae120bb652a1899b07742773b3f29d092252466e758e11b9936b8adb758ac098"
+              "url": "https://ghcr.io/v2/homebrew/core/yq/blobs/sha256:c5404881e9aba4d22663971dd620f7e8bbd2bbed07d6623ddcb06b8108eb8271",
+              "sha256": "c5404881e9aba4d22663971dd620f7e8bbd2bbed07d6623ddcb06b8108eb8271"
             },
             "arm64_ventura": {
               "cellar": ":any_skip_relocation",
-              "url": "https://ghcr.io/v2/homebrew/core/yq/blobs/sha256:420e9b4f7662ed6ffcbc01102030f30abd3b11aac811c61a285a74cb8b5b6f7b",
-              "sha256": "420e9b4f7662ed6ffcbc01102030f30abd3b11aac811c61a285a74cb8b5b6f7b"
+              "url": "https://ghcr.io/v2/homebrew/core/yq/blobs/sha256:ab37a388dac49f8aa1dee95154cf840cd4c23cd8756cf394dc629e647d908c8d",
+              "sha256": "ab37a388dac49f8aa1dee95154cf840cd4c23cd8756cf394dc629e647d908c8d"
             },
             "arm64_monterey": {
               "cellar": ":any_skip_relocation",
-              "url": "https://ghcr.io/v2/homebrew/core/yq/blobs/sha256:14882d182eefc14dc8b5697c24ea3e09df40c8ca45fb70536a17601f68ab0def",
-              "sha256": "14882d182eefc14dc8b5697c24ea3e09df40c8ca45fb70536a17601f68ab0def"
+              "url": "https://ghcr.io/v2/homebrew/core/yq/blobs/sha256:8580ba4cd20a0d5610dd253d91689d1fdacb5eb792ec2115713921524b8eb4ad",
+              "sha256": "8580ba4cd20a0d5610dd253d91689d1fdacb5eb792ec2115713921524b8eb4ad"
             },
             "sonoma": {
               "cellar": ":any_skip_relocation",
-              "url": "https://ghcr.io/v2/homebrew/core/yq/blobs/sha256:5b6c8d4678f9807cade82cddbb54365b3f79ffc6ff5d3ce995ebb6684a66d104",
-              "sha256": "5b6c8d4678f9807cade82cddbb54365b3f79ffc6ff5d3ce995ebb6684a66d104"
+              "url": "https://ghcr.io/v2/homebrew/core/yq/blobs/sha256:db2d0b23fcae3685db08dc78b67c592166ec4311f6058aad40fd984face94e60",
+              "sha256": "db2d0b23fcae3685db08dc78b67c592166ec4311f6058aad40fd984face94e60"
             },
             "ventura": {
               "cellar": ":any_skip_relocation",
-              "url": "https://ghcr.io/v2/homebrew/core/yq/blobs/sha256:43812cc640af7a5b695a34a1ccea048e40212864d054cd2177cdd2afbcfe502c",
-              "sha256": "43812cc640af7a5b695a34a1ccea048e40212864d054cd2177cdd2afbcfe502c"
+              "url": "https://ghcr.io/v2/homebrew/core/yq/blobs/sha256:823638d8a82d905fcd00c7e88b12cfe6ada9e9e4a9ea627cfb37d55965648354",
+              "sha256": "823638d8a82d905fcd00c7e88b12cfe6ada9e9e4a9ea627cfb37d55965648354"
             },
             "monterey": {
               "cellar": ":any_skip_relocation",
-              "url": "https://ghcr.io/v2/homebrew/core/yq/blobs/sha256:eef56bff54c49fce95472e0ad7ff3343c9b591d50c56bb2a3c5dfa929c10112e",
-              "sha256": "eef56bff54c49fce95472e0ad7ff3343c9b591d50c56bb2a3c5dfa929c10112e"
+              "url": "https://ghcr.io/v2/homebrew/core/yq/blobs/sha256:87ff086af7864d8419c519642079d6923cbc7931250faa39dd0df44a58ffcaf9",
+              "sha256": "87ff086af7864d8419c519642079d6923cbc7931250faa39dd0df44a58ffcaf9"
             },
             "x86_64_linux": {
               "cellar": ":any_skip_relocation",
-              "url": "https://ghcr.io/v2/homebrew/core/yq/blobs/sha256:4ad8aad7eaf0269ce1bca1996c958e3d96465748a34b86bd5993fed07b306003",
-              "sha256": "4ad8aad7eaf0269ce1bca1996c958e3d96465748a34b86bd5993fed07b306003"
+              "url": "https://ghcr.io/v2/homebrew/core/yq/blobs/sha256:2c42c4894c4508bd6af2551dd07e5fe5646fe0ecb25d0a96931a263b5a46fdc1",
+              "sha256": "2c42c4894c4508bd6af2551dd07e5fe5646fe0ecb25d0a96931a263b5a46fdc1"
             }
           }
         }
@@ -2705,6 +2690,10 @@
             }
           }
         }
+      },
+      "stripe/stripe-mock/stripe-mock": {
+        "version": "0.182.0",
+        "bottle": false
       }
     },
     "cask": {
@@ -2967,7 +2956,7 @@
         }
       },
       "font-victor-mono": {
-        "version": "1.5.5",
+        "version": "1.5.6",
         "options": {
           "full_name": "font-victor-mono"
         }
diff --git a/Gemfile b/Gemfile
index 066aaa77..373df874 100644
--- a/Gemfile
+++ b/Gemfile
@@ -36,6 +36,7 @@ gem 'twitter-bootstrap-rails'
 gem 'uglifier'
 gem 'ventable'
 gem 'yard'
+gem 'annotate'
 
 group :development, :test do
   gem 'codecov'
@@ -48,7 +49,6 @@ group :development, :test do
 end
 
 group :development do
-  gem 'annotate'
   gem 'asciidoctor'
   gem 'capistrano', '< 3'
 end
diff --git a/Gemfile.lock b/Gemfile.lock
index 53ed558b..1b129b0b 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -204,7 +204,7 @@ GEM
     parser (3.3.0.5)
       ast (~> 2.4.1)
       racc
-    pg (1.5.4)
+    pg (1.5.5)
     protected_attributes_continued (1.9.0)
       activemodel (>= 5.0)
     psych (5.1.2)
@@ -347,7 +347,7 @@ GEM
       sprockets (>= 3.0.0)
     ssrf_filter (1.1.2)
     stringio (3.1.0)
-    stripe (10.8.0)
+    stripe (10.9.0)
     stripe-ruby-mock (2.5.8)
       dante (>= 0.2.0)
       multi_json (~> 1.0)
diff --git a/app/models/application_record.rb b/app/models/application_record.rb
index 504a5dbf..10a4cba8 100644
--- a/app/models/application_record.rb
+++ b/app/models/application_record.rb
@@ -1,4 +1,3 @@
-
 class ApplicationRecord < ActiveRecord::Base
   self.abstract_class = true
 end
diff --git a/app/models/eald_payment.rb b/app/models/eald_payment.rb
index ad655c9d..de764a29 100644
--- a/app/models/eald_payment.rb
+++ b/app/models/eald_payment.rb
@@ -1,5 +1,24 @@
 # frozen_string_literal: true
 
+# == Schema Information
+#
+# Table name: eald_payments
+#
+#  id                    :bigint           not null, primary key
+#  amount_charged_cents  :integer          not null
+#  early_arrival_passes  :integer          default(0), not null
+#  email                 :string(255)      not null
+#  late_departure_passes :integer          default(0), not null
+#  name                  :string(255)      not null
+#  created_at            :datetime         not null
+#  updated_at            :datetime         not null
+#  event_id              :bigint
+#  stripe_charge_id      :string           not null
+#
+# Indexes
+#
+#  index_eald_payments_on_event_id  (event_id)
+#
 # Payment for early arrival/late departures passes.
 #
 # We only associate this with an event, as we want to treat these separately
diff --git a/app/models/event.rb b/app/models/event.rb
index dc069476..edd35be5 100644
--- a/app/models/event.rb
+++ b/app/models/event.rb
@@ -1,5 +1,33 @@
 # frozen_string_literal: true
 
+# == Schema Information
+#
+# Table name: events
+#
+#  id                            :bigint           not null, primary key
+#  adult_ticket_price            :decimal(8, 2)
+#  allow_donations               :boolean          default(FALSE), not null
+#  allow_financial_assistance    :boolean          default(FALSE), not null
+#  cabin_price                   :decimal(8, 2)
+#  early_arrival_price           :decimal(8, 2)    default(0.0)
+#  end_time                      :datetime
+#  kid_ticket_price              :decimal(8, 2)
+#  late_departure_price          :decimal(8, 2)    default(0.0)
+#  max_adult_tickets_per_request :integer
+#  max_cabin_requests            :integer
+#  max_cabins_per_request        :integer
+#  max_kid_tickets_per_request   :integer
+#  name                          :string
+#  photo                         :string
+#  require_mailing_address       :boolean          default(FALSE), not null
+#  start_time                    :datetime
+#  ticket_requests_end_time      :datetime
+#  ticket_sales_end_time         :datetime
+#  ticket_sales_start_time       :datetime
+#  tickets_require_approval      :boolean          default(TRUE), not null
+#  created_at                    :datetime         not null
+#  updated_at                    :datetime         not null
+#
 # Core object containing all information related to an actual event being held.
 class Event < ApplicationRecord
   has_many :event_admins
diff --git a/app/models/event_admin.rb b/app/models/event_admin.rb
index bfd635ef..408a2c09 100644
--- a/app/models/event_admin.rb
+++ b/app/models/event_admin.rb
@@ -1,5 +1,22 @@
 # frozen_string_literal: true
 
+# == Schema Information
+#
+# Table name: event_admins
+#
+#  id         :bigint           not null, primary key
+#  created_at :datetime         not null
+#  updated_at :datetime         not null
+#  event_id   :bigint
+#  user_id    :bigint
+#
+# Indexes
+#
+#  index_event_admins_on_event_id              (event_id)
+#  index_event_admins_on_event_id_and_user_id  (event_id,user_id) UNIQUE
+#  index_event_admins_on_user_id               (user_id)
+#  index_event_admins_on_user_id_only          (user_id)
+#
 class EventAdmin < ApplicationRecord
   attr_accessible :event_id, :user_id
 
diff --git a/app/models/job.rb b/app/models/job.rb
index cddd2830..26f3557f 100644
--- a/app/models/job.rb
+++ b/app/models/job.rb
@@ -1,5 +1,20 @@
 # frozen_string_literal: true
 
+# == Schema Information
+#
+# Table name: jobs
+#
+#  id          :bigint           not null, primary key
+#  description :string(512)      not null
+#  name        :string(100)      not null
+#  created_at  :datetime         not null
+#  updated_at  :datetime         not null
+#  event_id    :bigint           not null
+#
+# Indexes
+#
+#  index_jobs_on_event_id  (event_id)
+#
 class Job < ApplicationRecord
   belongs_to :event
   has_many :time_slots, dependent: :destroy
diff --git a/app/models/payment.rb b/app/models/payment.rb
index 83d85d2b..61b95272 100644
--- a/app/models/payment.rb
+++ b/app/models/payment.rb
@@ -1,5 +1,17 @@
 # frozen_string_literal: true
 
+# == Schema Information
+#
+# Table name: payments
+#
+#  id                :bigint           not null, primary key
+#  explanation       :string
+#  status            :string(1)        default("P"), not null
+#  created_at        :datetime         not null
+#  updated_at        :datetime         not null
+#  stripe_charge_id  :string(255)
+#  ticket_request_id :integer          not null
+#
 class Payment < ApplicationRecord
   include PaymentsHelper
 
diff --git a/app/models/price_rule.rb b/app/models/price_rule.rb
index c1b011d3..f5ba5445 100644
--- a/app/models/price_rule.rb
+++ b/app/models/price_rule.rb
@@ -1,5 +1,21 @@
 # frozen_string_literal: true
 
+# == Schema Information
+#
+# Table name: price_rules
+#
+#  id            :bigint           not null, primary key
+#  price         :decimal(8, 2)
+#  trigger_value :integer
+#  type          :string
+#  created_at    :datetime         not null
+#  updated_at    :datetime         not null
+#  event_id      :bigint
+#
+# Indexes
+#
+#  index_price_rules_on_event_id  (event_id)
+#
 class PriceRule < ApplicationRecord
   belongs_to :event
 
diff --git a/app/models/price_rule/kids_equal_to.rb b/app/models/price_rule/kids_equal_to.rb
index 3f90457d..93521fbb 100644
--- a/app/models/price_rule/kids_equal_to.rb
+++ b/app/models/price_rule/kids_equal_to.rb
@@ -1,5 +1,21 @@
 # frozen_string_literal: true
 
+# == Schema Information
+#
+# Table name: price_rules
+#
+#  id            :bigint           not null, primary key
+#  price         :decimal(8, 2)
+#  trigger_value :integer
+#  type          :string
+#  created_at    :datetime         not null
+#  updated_at    :datetime         not null
+#  event_id      :bigint
+#
+# Indexes
+#
+#  index_price_rules_on_event_id  (event_id)
+#
 # Applied when a ticket request has indicated that they are bringing a specific
 # number of kids.
 class PriceRule
diff --git a/app/models/shift.rb b/app/models/shift.rb
index 149633d4..867e45e4 100644
--- a/app/models/shift.rb
+++ b/app/models/shift.rb
@@ -1,5 +1,21 @@
 # frozen_string_literal: true
 
+# == Schema Information
+#
+# Table name: shifts
+#
+#  id           :bigint           not null, primary key
+#  name         :string(70)
+#  created_at   :datetime         not null
+#  updated_at   :datetime         not null
+#  time_slot_id :bigint           not null
+#  user_id      :bigint           not null
+#
+# Indexes
+#
+#  index_shifts_on_time_slot_id  (time_slot_id)
+#  index_shifts_on_user_id       (user_id)
+#
 class Shift < ApplicationRecord
   belongs_to :time_slot
   belongs_to :user
diff --git a/app/models/site_admin.rb b/app/models/site_admin.rb
index e4439035..45fe38e3 100644
--- a/app/models/site_admin.rb
+++ b/app/models/site_admin.rb
@@ -1,5 +1,14 @@
 # frozen_string_literal: true
 
+# == Schema Information
+#
+# Table name: site_admins
+#
+#  id         :bigint           not null, primary key
+#  created_at :datetime         not null
+#  updated_at :datetime         not null
+#  user_id    :integer          not null
+#
 class SiteAdmin < ApplicationRecord
   attr_accessible :user_id
 
diff --git a/app/models/ticket_request.rb b/app/models/ticket_request.rb
index 2b4d6c13..ba3437a2 100644
--- a/app/models/ticket_request.rb
+++ b/app/models/ticket_request.rb
@@ -1,5 +1,39 @@
 # frozen_string_literal: true
 
+# == Schema Information
+#
+# Table name: ticket_requests
+#
+#  id                      :bigint           not null, primary key
+#  address_line1           :string(200)
+#  address_line2           :string(200)
+#  admin_notes             :string(512)
+#  adults                  :integer          default(1), not null
+#  agrees_to_terms         :boolean
+#  cabins                  :integer          default(0), not null
+#  car_camping             :boolean
+#  car_camping_explanation :string(200)
+#  city                    :string(50)
+#  country_code            :string(4)
+#  donation                :decimal(8, 2)    default(0.0)
+#  early_arrival_passes    :integer          default(0), not null
+#  guests                  :text
+#  kids                    :integer          default(0), not null
+#  late_departure_passes   :integer          default(0), not null
+#  needs_assistance        :boolean          default(FALSE), not null
+#  notes                   :string(500)
+#  previous_contribution   :string(250)
+#  role                    :string           default("volunteer"), not null
+#  role_explanation        :string(200)
+#  special_price           :decimal(8, 2)
+#  state                   :string(50)
+#  status                  :string(1)        not null
+#  zip_code                :string(32)
+#  created_at              :datetime         not null
+#  updated_at              :datetime         not null
+#  event_id                :integer          not null
+#  user_id                 :integer          not null
+#
 # Individual request for one or more tickets.
 # This is intended to capture as much information as possible about the ticket,
 # as well as the state of the request.
diff --git a/app/models/time_slot.rb b/app/models/time_slot.rb
index b919d022..a1b22068 100644
--- a/app/models/time_slot.rb
+++ b/app/models/time_slot.rb
@@ -1,5 +1,21 @@
 # frozen_string_literal: true
 
+# == Schema Information
+#
+# Table name: time_slots
+#
+#  id         :bigint           not null, primary key
+#  end_time   :datetime         not null
+#  slots      :integer          not null
+#  start_time :datetime         not null
+#  created_at :datetime         not null
+#  updated_at :datetime         not null
+#  job_id     :bigint           not null
+#
+# Indexes
+#
+#  index_time_slots_on_job_id  (job_id)
+#
 class TimeSlot < ApplicationRecord
   belongs_to :job
   has_many :shifts, dependent: :destroy
diff --git a/app/models/user.rb b/app/models/user.rb
index c5c6951a..6e08938e 100644
--- a/app/models/user.rb
+++ b/app/models/user.rb
@@ -1,5 +1,39 @@
 # frozen_string_literal: true
 
+# == Schema Information
+#
+# Table name: users
+#
+#  id                     :bigint           not null, primary key
+#  authentication_token   :string(64)
+#  confirmation_sent_at   :datetime
+#  confirmation_token     :string
+#  confirmed_at           :datetime
+#  current_sign_in_at     :datetime
+#  current_sign_in_ip     :string
+#  email                  :string           not null
+#  encrypted_password     :string           not null
+#  failed_attempts        :integer          default(0)
+#  last_sign_in_at        :datetime
+#  last_sign_in_ip        :string
+#  locked_at              :datetime
+#  name                   :string(70)       not null
+#  remember_created_at    :datetime
+#  reset_password_sent_at :datetime
+#  reset_password_token   :string
+#  sign_in_count          :integer          default(0)
+#  unconfirmed_email      :string
+#  unlock_token           :string
+#  created_at             :datetime         not null
+#  updated_at             :datetime         not null
+#
+# Indexes
+#
+#  index_users_on_confirmation_token    (confirmation_token) UNIQUE
+#  index_users_on_email                 (email) UNIQUE
+#  index_users_on_reset_password_token  (reset_password_token) UNIQUE
+#  index_users_on_unlock_token          (unlock_token) UNIQUE
+#
 require 'securerandom'
 
 # A real-life living breathing human.
diff --git a/bin/boot-up b/bin/boot-up
index f4df534f..2ead1114 100755
--- a/bin/boot-up
+++ b/bin/boot-up
@@ -16,226 +16,9 @@ export BASHMATIC_HOME="${BASHMATIC_HOME:-"${HOME}/.bashmatic"}"
 source "${BASHMATIC_HOME}/init.sh" >/dev/null 2>&1
 output.constrain-screen-width 100
 
-export default_bundler_version="1.17.3"
-export python_version="2.7.18"
-export python_major_version="$(echo "${python_version}" | cut -d '.' -f 1)"
-
-export ruby_version="$(cat .ruby-version | tr -d '\n')"
-
-function ensure-postgresql() {
-  [[ -n "$( ps -ef | grep "[p]ostg" )" ]] && pg_isready >/dev/null && {
-    success "PostgreSQL is already running."
-    return 0
-  }
-
-  (command -v brew >/dev/null) && {
-    run.set-all continue-on-error
-
-    h1 "Installing and starting PostgreSQL using Homebrew..."
-
-    run "brew install postgresql@14"
-    run "brew link postgresql@14"
-    run "brew services start postgresql@14"
-
-    sleep 3
-
-    pg_isready && success "Database is UP."
-    pg_isready || {
-      error "Unable to start PostgreSQL. Please install it manually" \
-        "from: https://www.postgresql.org/download/"
-      open "https://www.postgresql.org/download/"
-      exit 1
-    }
-
-    run "createuser -s postgres -U ${USER}"
-    run "createuser -s root -U ${USER}"
-  }
-}
-
-function ensure-stripe-mock() {
-  run.set-all continue-on-error
-  run "brew install stripe/stripe-mock/stripe-mock"
-  run "brew upgrade stripe-mock"
-  run "brew services start stripe-mock"
-}
-
-function ensure-python() {
-  local local_python_version
-  local -a version_parts
-  run.set-all continue-on-error
-  command -v python >/dev/null && {
-    version_parts=( $(python -c 'import sys; print(sys.version_info[0])' | tr '.' ' ') )
-  }
-
-  local_python_version="${version_parts[0]}"
-
-  if [[ ${local_python_version} -eq ${python_major_version} ]]; then
-    success "Python ${python_version} is already installed."
-    return 0
-  else
-    h1 "Installing Python ${python_version} using pyenv..."
-    command -v pyenv >/dev/null || run "brew install pyenv"
-    eval "$(pyenv init -)"
-    run "pyenv install -s ${python_version}"
-    run "pyenv global ${python_version}"
-  fi
-}
-
-function ensure-ruby-via-ruby-install() {
-  run "brew install ruby-install --formulae"
-  export CFLAGS="-Wno-error=implicit-function-declaration"
-  run "mkdir -p ${HOME}/.rbenv/versions"
-  run "ruby-install --install-dir ${HOME}/.rbenv/versions ${ruby_version} -- --enable-shared"
-}
-
-
-function ensure-ruby-via-rbenv() {
-  export CFLAGS="-Wno-error=implicit-function-declaration"
-  run "rbenv install -s ${ruby_version}"
-}
-
-function ensure-ruby() {
-  h2 "Ensuring Ruby & Gems are Installed..."
-  if command -v rbenv >/dev/null; then
-    run "brew upgrade rbenv ruby-build"
-  else
-    run "brew install rbenv ruby-build"
-  fi
-
-  eval "$(rbenv init -)"
-
-  local bundler_version=$(gem.gemfile.bundler-version)
-  test -z "${bundler_version}" && bundler_version="${default_bundler_version}"
-
-  if ${use_ruby_install}; then
-    ensure-ruby-via-ruby-install
-  else
-    ensure-ruby-via-rbenv
-  fi
-}
-
-
-function ensure-bundle() {
-  h2 "Installing Dependent Gems..."
-  run "gem install bundler --version ${bundler_version} -N"
-
-  run "bundle config set          --local path 'vendor/bundle'"
-  run "bundle config pg           --with-pg-config=$(command -v pg_config)"
-  run "bundle config libv8        --with-system-v8"
-  run "bundle config therubyracer --with-v8-dir=$(brew --prefix)/opt/v8@3.15"
-  run "bundle check || bundle install -j 12 || bundler update --bundler && bundle install"
-
-  h2 "Creating Databases & Running Tests"
-  run "bundle exec rake db:create"
-  run "bundle exec rake db:migrate db:seed"
-  run "bundle exec rake db:test:prepare"
-  run.set-next show-output-on
-  run "bundle exec rspec"
-}
-
-function puma-pids() {
-  # shellcheck disable=SC2009
-  ps -ef | grep "[p]uma" | cut -d ' ' -f 4
-}
-
-function puma-running() {
-  netstat -an | grep LISTEN | grep -q 3000
-}
-
-# shellcheck disable=SC2207
-function kill-puma() {
-  local counter=0
-  while puma-running; do
-    counter=$((counter + 1))
-    if [[ ${counter} -gt 10 ]]; then
-      .err "Too many attempts to kill puma, please whack it manually."
-      exit 1
-    fi
-    local -a pids=($(puma-pids))
-    if [[ ${#pids[@]} -gt 0 ]]; then
-      set +e
-      kill -TERM "${pids[@]}"
-      sleep 5
-      pids=($(puma-pids))
-      [[ ${#pids[@]} -gt 0 ]] && {
-        kill -KILL "${pids[@]}"
-        sleep 2
-      }
-    fi
-  done
-}
-
-function .err() {
-  printf -- "\n${bakred} 🖕 ${clr}${txtred}${clr} ${txtred}${clr}${bakred} %s ${clr}${txtred}${clr}\n" "$*"
-}
-
-function .inf() {
-  printf -- "${bakgrn}  ️✔︎ ${clr}${txtgrn}${clr} ${txtylw}%s....${clr}\n" "$*"
-}
-
-function setup() {
-  export MAKE_ENV=".make.env"
-  cat <<EOF >>"${MAKE_ENV}"
-export RUBYOPT="-W0"
-export MALLOC_ARENA_MAX=2
-EOF
-
-  eval "$(cat "${MAKE_ENV}")"
-
-  local v8pkg="$(brew list | grep v8)"
-  [[ -z "${v8pkg}" || ${v8pkg} == "v8" ]] && brew uninstall v8 >/dev/null 2>&1
-
-  run "brew list | grep -q v8@3.15 || brew install v8@3.15 2>/dev/null"
-
-  ensure-postgresql     || exit 1
-  ensure-ruby           || exit 4
-  ensure-python         || exit 3
-  ensure-bundle         || exit 5
-  ensure-stripe-mock    || exit 6
-  return 0
-}
-
-function main() {
-  setup
-
-  if [[ -z "${RAILS_ENV}" ]]; then
-    .err "RAILS_ENV must be set prior to calling this script."
-    echo
-    .inf "To boot the application via the 'make' target, run one of the: "
-    echo
-    .inf '		make development boot'
-    .inf '		make staging     boot'
-    .inf '		make production  boot'
-    echo
-    exit 1
-  else
-    .inf "Starting with RAILS_ENV=${RAILS_ENV}"
-  fi
-
-  puma-running && {
-    .err "It appears that port 3000 is taken by something..."
-    exit 1
-  }
-  .inf "Starting Puma on port 3000"
-  (sleep 8 && open "http://127.0.0.1:3000") &
-  run.set-next show-output-on
-  run "bundle exec puma -C config/puma.rb"
-  rm -f "${MAKE_ENV}"
-}
-
-export use_ruby_install=false
-
-[[ "$1" == "-h" || "$1" == "--help" ]] && {
-  echo "Usage: $0 [--source] [--ruby-install]"
-  echo
-  echo "  --source        -  load the source code of this script but don't run main()"
-  echo "  --ruby-install  -  Use ruby-install to build ruby instead of rbenv"
-  echo
-  exit 0
-}
-
-[[ "$*" =~ "--ruby-install" ]] && use_ruby_install=true
-
-[[ "$1" == "--source" ]] || main "$@"
-
-
+run "brew bundle --no-upgrade --no-lock"
+run "rbenv install -s $(cat .ruby-version)"
+run "mkdir -p .bundle"
+run "cp development/config/config.Darwin.arm64 .bundle/config"
+run "bundle install -j 12"
+run "bin/rails db:migrate"
diff --git a/config/environments/development.rb b/config/environments/development.rb
index fd940bf3..debf91f5 100644
--- a/config/environments/development.rb
+++ b/config/environments/development.rb
@@ -13,7 +13,7 @@
 
   config.autoloader = :zeitwerk
 
-  # config.eager_load = false
+  config.eager_load = false
 
   # Show full error reports and disable caching
   config.consider_all_requests_local       = true
diff --git a/config/environments/test.rb b/config/environments/test.rb
index ed58c357..2e15c540 100644
--- a/config/environments/test.rb
+++ b/config/environments/test.rb
@@ -9,7 +9,7 @@
   # and recreated between test runs. Don't rely on the data there!
   config.cache_classes = false
 
-  config.eager_load = true
+  config.eager_load = false
 
   # Prepend all log lines with the following tags
   config.log_tags = [->(_req) { DateTime.now }, :uuid]
diff --git a/config/initializers/auto_annotate_models.rb b/config/initializers/auto_annotate_models.rb
new file mode 100644
index 00000000..dc98c888
--- /dev/null
+++ b/config/initializers/auto_annotate_models.rb
@@ -0,0 +1,47 @@
+Annotate.set_defaults(
+  'active_admin' => 'false',
+  'additional_file_patterns' => [],
+  'routes' => 'false',
+  'models' => 'true',
+  'position_in_routes' => 'before',
+  'position_in_class' => 'before',
+  'position_in_test' => 'before',
+  'position_in_fixture' => 'before',
+  'position_in_factory' => 'before',
+  'position_in_serializer' => 'before',
+  'show_foreign_keys' => 'true',
+  'show_complete_foreign_keys' => 'false',
+  'show_indexes' => 'true',
+  'simple_indexes' => 'false',
+  'model_dir' => 'app/models',
+  'root_dir' => '',
+  'include_version' => 'false',
+  'require' => '',
+  'exclude_tests' => 'false',
+  'exclude_fixtures' => 'false',
+  'exclude_factories' => 'false',
+  'exclude_serializers' => 'false',
+  'exclude_scaffolds' => 'true',
+  'exclude_controllers' => 'true',
+  'exclude_helpers' => 'true',
+  'exclude_sti_subclasses' => 'false',
+  'ignore_model_sub_dir' => 'false',
+  'ignore_columns' => nil,
+  'ignore_routes' => nil,
+  'ignore_unknown_models' => 'false',
+  'hide_limit_column_types' => 'integer,bigint,boolean',
+  'hide_default_column_types' => 'json,jsonb,hstore',
+  'skip_on_db_migrate' => 'false',
+  'format_bare' => 'true',
+  'format_rdoc' => 'false',
+  'format_yard' => 'false',
+  'format_markdown' => 'false',
+  'sort' => 'false',
+  'force' => 'false',
+  'frozen' => 'false',
+  'classified_sort' => 'true',
+  'trace' => 'false',
+  'wrapper_open' => nil,
+  'wrapper_close' => nil,
+  'with_comment' => 'true'
+)
diff --git a/development/config/config.Darwin.arm64 b/development/config/config.Darwin.arm64
new file mode 100644
index 00000000..6bd584b8
--- /dev/null
+++ b/development/config/config.Darwin.arm64
@@ -0,0 +1,9 @@
+---
+BUNDLE_JOBS: "12"
+BUNDLE_BUILD__PG: "--with-pg-config=/opt/homebrew/opt/postgresql@15/bin/pg_config"
+BUNDLE_BUILD__LIBV8: "--with-system-v8"
+BUNDLE_BUILD__FFI: "--with-v8-dir=/opt/homebrew/opt/v8"
+BUNDLE_BUILD__THERUBYRACER: "--with-v8-dir=/opt/homebrew/opt/v8"
+BUNDLE_ENTERPRISE__CONTRIBSYS__COM: "c07fa39b:1c6f45bc"
+BUNDLE_BUILD: "--with-cflags=-Wno-error=implicit-function-declaration --with-cppflags=-Wno-warning=compound-token-split-by-macro"
+BUNDLE_GEMFILE: "Gemfile"
diff --git a/lib/tasks/auto_annotate_models.rake b/lib/tasks/auto_annotate_models.rake
new file mode 100644
index 00000000..e96283ea
--- /dev/null
+++ b/lib/tasks/auto_annotate_models.rake
@@ -0,0 +1,59 @@
+# NOTE: only doing this in development as some production environments (Heroku)
+# NOTE: are sensitive to local FS writes, and besides -- it's just not proper
+# NOTE: to have a dev-mode tool do its thing in production.
+if Rails.env.development?
+  require 'annotate'
+  task :set_annotation_options do
+    # You can override any of these by setting an environment variable of the
+    # same name.
+    Annotate.set_defaults(
+      'active_admin'                => 'false',
+      'additional_file_patterns'    => [],
+      'routes'                      => 'false',
+      'models'                      => 'true',
+      'position_in_routes'          => 'before',
+      'position_in_class'           => 'before',
+      'position_in_test'            => 'before',
+      'position_in_fixture'         => 'before',
+      'position_in_factory'         => 'before',
+      'position_in_serializer'      => 'before',
+      'show_foreign_keys'           => 'true',
+      'show_complete_foreign_keys'  => 'false',
+      'show_indexes'                => 'true',
+      'simple_indexes'              => 'false',
+      'model_dir'                   => 'app/models',
+      'root_dir'                    => '',
+      'include_version'             => 'false',
+      'require'                     => '',
+      'exclude_tests'               => 'false',
+      'exclude_fixtures'            => 'false',
+      'exclude_factories'           => 'false',
+      'exclude_serializers'         => 'false',
+      'exclude_scaffolds'           => 'true',
+      'exclude_controllers'         => 'true',
+      'exclude_helpers'             => 'true',
+      'exclude_sti_subclasses'      => 'false',
+      'ignore_model_sub_dir'        => 'false',
+      'ignore_columns'              => nil,
+      'ignore_routes'               => nil,
+      'ignore_unknown_models'       => 'false',
+      'hide_limit_column_types'     => 'integer,bigint,boolean',
+      'hide_default_column_types'   => 'json,jsonb,hstore',
+      'skip_on_db_migrate'          => 'false',
+      'format_bare'                 => 'true',
+      'format_rdoc'                 => 'false',
+      'format_yard'                 => 'false',
+      'format_markdown'             => 'false',
+      'sort'                        => 'false',
+      'force'                       => 'false',
+      'frozen'                      => 'false',
+      'classified_sort'             => 'true',
+      'trace'                       => 'false',
+      'wrapper_open'                => nil,
+      'wrapper_close'               => nil,
+      'with_comment'                => 'true'
+    )
+  end
+
+  Annotate.load_tasks
+end
diff --git a/spec/controllers/emails_controller_spec.rb b/spec/controllers/emails_controller_spec.rb
index 7ed216f5..0675d5dd 100644
--- a/spec/controllers/emails_controller_spec.rb
+++ b/spec/controllers/emails_controller_spec.rb
@@ -1,7 +1,5 @@
 # frozen_string_literal: true
 
-require 'spec_helper'
-
 describe EmailsController do
   describe 'GET #index' do
     let(:email) { nil }
diff --git a/spec/controllers/events_controller_spec.rb b/spec/controllers/events_controller_spec.rb
index 054ec99d..54b35aad 100644
--- a/spec/controllers/events_controller_spec.rb
+++ b/spec/controllers/events_controller_spec.rb
@@ -1,7 +1,5 @@
 # frozen_string_literal: true
 
-require 'spec_helper'
-
 describe EventsController do
   let(:event) { Event.make! }
   let(:viewer) { nil }
diff --git a/spec/controllers/ticket_requests_controller_spec.rb b/spec/controllers/ticket_requests_controller_spec.rb
index c888c552..04c37c23 100644
--- a/spec/controllers/ticket_requests_controller_spec.rb
+++ b/spec/controllers/ticket_requests_controller_spec.rb
@@ -1,7 +1,5 @@
 # frozen_string_literal: true
 
-require 'spec_helper'
-
 describe TicketRequestsController do
   let(:viewer) { nil }
 
diff --git a/spec/factories/event.rb b/spec/factories/event.rb
index 9dbeb40c..070bb842 100644
--- a/spec/factories/event.rb
+++ b/spec/factories/event.rb
@@ -6,7 +6,7 @@
     start_time { 1.year.from_now }
     end_time { 1.year.from_now + 1.day }
 
-    adult_ticket_price { Random.rand(0..100) }
+    adult_ticket_price { Random.rand(100) }
     kid_ticket_price { nil }
     cabin_price { nil }
     max_adult_tickets_per_request { Random.rand(1..4) }
@@ -20,7 +20,7 @@
 
     trait :cabins_available do
       cabin_price { Random.rand(100) }
-      max_cabins_per_request { Random.rand(1..1) }
+      max_cabins_per_request { Random.rand(1...1) }
     end
   end
 end
diff --git a/spec/lib/fnf/csv_reader_spec.rb b/spec/lib/fnf/csv_reader_spec.rb
index 4f7832b8..61076de1 100644
--- a/spec/lib/fnf/csv_reader_spec.rb
+++ b/spec/lib/fnf/csv_reader_spec.rb
@@ -1,6 +1,5 @@
 # frozen_string_literal: true
 
-require 'spec_helper'
 require 'fnf/csv_reader'
 
 module FnF
diff --git a/spec/lib/fnf/event_reporter_spec.rb b/spec/lib/fnf/event_reporter_spec.rb
index 73efd744..1f7ec137 100644
--- a/spec/lib/fnf/event_reporter_spec.rb
+++ b/spec/lib/fnf/event_reporter_spec.rb
@@ -1,6 +1,5 @@
 # frozen_string_literal: true
 
-require 'spec_helper'
 require 'fnf/csv_reader'
 
 module FnF
diff --git a/spec/lib/fnf/events/events_spec.rb b/spec/lib/fnf/events/events_spec.rb
index 660d0274..2b3dd2a1 100644
--- a/spec/lib/fnf/events/events_spec.rb
+++ b/spec/lib/fnf/events/events_spec.rb
@@ -1,7 +1,5 @@
 # frozen_string_literal: true
 
-require 'spec_helper'
-
 class Worker
   @events = {}
 
diff --git a/spec/lib/fnf/html_generator_spec.rb b/spec/lib/fnf/html_generator_spec.rb
index 323d0e01..a2f436b1 100644
--- a/spec/lib/fnf/html_generator_spec.rb
+++ b/spec/lib/fnf/html_generator_spec.rb
@@ -1,6 +1,5 @@
 # frozen_string_literal: true
 
-require 'spec_helper'
 require 'fnf/html_generator'
 
 module FnF
diff --git a/spec/lib/fnf/music_submissions_spec.rb b/spec/lib/fnf/music_submissions_spec.rb
index be93982e..db5e5d61 100644
--- a/spec/lib/fnf/music_submissions_spec.rb
+++ b/spec/lib/fnf/music_submissions_spec.rb
@@ -2,7 +2,6 @@
 
 require 'rspec'
 require 'tempfile'
-require 'spec_helper'
 
 RSpec.describe 'bin/music-submissions' do
   subject { File.read(result) }
diff --git a/spec/mailers/payment_mailer_spec.rb b/spec/mailers/payment_mailer_spec.rb
index 2715a7b5..a962853f 100644
--- a/spec/mailers/payment_mailer_spec.rb
+++ b/spec/mailers/payment_mailer_spec.rb
@@ -1,7 +1,5 @@
 # frozen_string_literal: true
 
-require 'spec_helper'
-
 describe PaymentMailer do
   let(:user) { User.make! }
   let(:event) { Event.make! name: 'Test Event' }
diff --git a/spec/mailers/ticket_request_mailer_spec.rb b/spec/mailers/ticket_request_mailer_spec.rb
index ac6ce4d0..ba9b7139 100644
--- a/spec/mailers/ticket_request_mailer_spec.rb
+++ b/spec/mailers/ticket_request_mailer_spec.rb
@@ -1,7 +1,5 @@
 # frozen_string_literal: true
 
-require 'spec_helper'
-
 describe TicketRequestMailer do
   let(:user) { User.make! }
   let(:event) { Event.make! name: 'Test Event' }
diff --git a/spec/models/event_admin_spec.rb b/spec/models/event_admin_spec.rb
index 9df7716b..606bf59e 100644
--- a/spec/models/event_admin_spec.rb
+++ b/spec/models/event_admin_spec.rb
@@ -1,7 +1,22 @@
 # frozen_string_literal: true
 
-require 'spec_helper'
-
+# == Schema Information
+#
+# Table name: event_admins
+#
+#  id         :bigint           not null, primary key
+#  created_at :datetime         not null
+#  updated_at :datetime         not null
+#  event_id   :bigint
+#  user_id    :bigint
+#
+# Indexes
+#
+#  index_event_admins_on_event_id              (event_id)
+#  index_event_admins_on_event_id_and_user_id  (event_id,user_id) UNIQUE
+#  index_event_admins_on_user_id               (user_id)
+#  index_event_admins_on_user_id_only          (user_id)
+#
 describe EventAdmin do
   describe 'validations' do
     describe '#user' do
diff --git a/spec/models/event_spec.rb b/spec/models/event_spec.rb
index 0bbb33b4..61383f39 100644
--- a/spec/models/event_spec.rb
+++ b/spec/models/event_spec.rb
@@ -1,7 +1,33 @@
 # frozen_string_literal: true
 
-require 'spec_helper'
-
+# == Schema Information
+#
+# Table name: events
+#
+#  id                            :bigint           not null, primary key
+#  adult_ticket_price            :decimal(8, 2)
+#  allow_donations               :boolean          default(FALSE), not null
+#  allow_financial_assistance    :boolean          default(FALSE), not null
+#  cabin_price                   :decimal(8, 2)
+#  early_arrival_price           :decimal(8, 2)    default(0.0)
+#  end_time                      :datetime
+#  kid_ticket_price              :decimal(8, 2)
+#  late_departure_price          :decimal(8, 2)    default(0.0)
+#  max_adult_tickets_per_request :integer
+#  max_cabin_requests            :integer
+#  max_cabins_per_request        :integer
+#  max_kid_tickets_per_request   :integer
+#  name                          :string
+#  photo                         :string
+#  require_mailing_address       :boolean          default(FALSE), not null
+#  start_time                    :datetime
+#  ticket_requests_end_time      :datetime
+#  ticket_sales_end_time         :datetime
+#  ticket_sales_start_time       :datetime
+#  tickets_require_approval      :boolean          default(TRUE), not null
+#  created_at                    :datetime         not null
+#  updated_at                    :datetime         not null
+#
 describe Event do
   it 'has a valid factory' do
     described_class.make.should be_valid
diff --git a/spec/models/site_admin_spec.rb b/spec/models/site_admin_spec.rb
index 1a6f95eb..20c2aa20 100644
--- a/spec/models/site_admin_spec.rb
+++ b/spec/models/site_admin_spec.rb
@@ -1,7 +1,14 @@
 # frozen_string_literal: true
 
-require 'spec_helper'
-
+# == Schema Information
+#
+# Table name: site_admins
+#
+#  id         :bigint           not null, primary key
+#  created_at :datetime         not null
+#  updated_at :datetime         not null
+#  user_id    :integer          not null
+#
 describe SiteAdmin do
   describe 'validations' do
     describe '#user' do
diff --git a/spec/models/ticket_request_spec.rb b/spec/models/ticket_request_spec.rb
index 4adc305b..3bcb8073 100644
--- a/spec/models/ticket_request_spec.rb
+++ b/spec/models/ticket_request_spec.rb
@@ -1,7 +1,39 @@
 # frozen_string_literal: true
 
-require 'spec_helper'
-
+# == Schema Information
+#
+# Table name: ticket_requests
+#
+#  id                      :bigint           not null, primary key
+#  address_line1           :string(200)
+#  address_line2           :string(200)
+#  admin_notes             :string(512)
+#  adults                  :integer          default(1), not null
+#  agrees_to_terms         :boolean
+#  cabins                  :integer          default(0), not null
+#  car_camping             :boolean
+#  car_camping_explanation :string(200)
+#  city                    :string(50)
+#  country_code            :string(4)
+#  donation                :decimal(8, 2)    default(0.0)
+#  early_arrival_passes    :integer          default(0), not null
+#  guests                  :text
+#  kids                    :integer          default(0), not null
+#  late_departure_passes   :integer          default(0), not null
+#  needs_assistance        :boolean          default(FALSE), not null
+#  notes                   :string(500)
+#  previous_contribution   :string(250)
+#  role                    :string           default("volunteer"), not null
+#  role_explanation        :string(200)
+#  special_price           :decimal(8, 2)
+#  state                   :string(50)
+#  status                  :string(1)        not null
+#  zip_code                :string(32)
+#  created_at              :datetime         not null
+#  updated_at              :datetime         not null
+#  event_id                :integer          not null
+#  user_id                 :integer          not null
+#
 describe TicketRequest do
   describe 'validations' do
     subject { ticket_request }
diff --git a/spec/models/user_spec.rb b/spec/models/user_spec.rb
index 7cc2ccf4..0d4887fe 100644
--- a/spec/models/user_spec.rb
+++ b/spec/models/user_spec.rb
@@ -1,7 +1,39 @@
 # frozen_string_literal: true
 
-require 'spec_helper'
-
+# == Schema Information
+#
+# Table name: users
+#
+#  id                     :bigint           not null, primary key
+#  authentication_token   :string(64)
+#  confirmation_sent_at   :datetime
+#  confirmation_token     :string
+#  confirmed_at           :datetime
+#  current_sign_in_at     :datetime
+#  current_sign_in_ip     :string
+#  email                  :string           not null
+#  encrypted_password     :string           not null
+#  failed_attempts        :integer          default(0)
+#  last_sign_in_at        :datetime
+#  last_sign_in_ip        :string
+#  locked_at              :datetime
+#  name                   :string(70)       not null
+#  remember_created_at    :datetime
+#  reset_password_sent_at :datetime
+#  reset_password_token   :string
+#  sign_in_count          :integer          default(0)
+#  unconfirmed_email      :string
+#  unlock_token           :string
+#  created_at             :datetime         not null
+#  updated_at             :datetime         not null
+#
+# Indexes
+#
+#  index_users_on_confirmation_token    (confirmation_token) UNIQUE
+#  index_users_on_email                 (email) UNIQUE
+#  index_users_on_reset_password_token  (reset_password_token) UNIQUE
+#  index_users_on_unlock_token          (unlock_token) UNIQUE
+#
 describe User do
   it 'has a valid factory' do
     described_class.make.should be_valid
diff --git a/spec/spec_helper.rb b/spec/spec_helper.rb
index a82ad594..d32a41b2 100644
--- a/spec/spec_helper.rb
+++ b/spec/spec_helper.rb
@@ -3,7 +3,6 @@
 ENV['RAILS_ENV'] = 'test'
 
 require 'simplecov'
-require 'codecov' if ENV['CODECOV_TOKEN']
 SimpleCov.start 'rails'
 
 require File.expand_path('../config/environment', __dir__)