diff --git a/.planning/phases/01-semantic-position-model/01-01-PLAN.md b/.planning/phases/01-semantic-position-model/01-01-PLAN.md
index 863af5b..f16261d 100644
--- a/.planning/phases/01-semantic-position-model/01-01-PLAN.md
+++ b/.planning/phases/01-semantic-position-model/01-01-PLAN.md
@@ -11,9 +11,9 @@ autonomous: true
 
 must_haves:
   truths:
-    - "Games get sortOrder derived from game time (minutes since midnight + offset)"
-    - "Inserting between two items produces midpoint sortOrder"
-    - "Day number can be calculated from any date given trip start date"
+    - "Games sort by schedule time within each day"
+    - "Items can be inserted at any position (before, between, after existing items)"
+    - "Items can be assigned to any trip day by date calculation"
   artifacts:
     - path: "SportsTime/Core/Models/Domain/SortOrderProvider.swift"
       provides: "sortOrder calculation utilities"
@@ -21,11 +21,7 @@ must_haves:
     - path: "SportsTime/Core/Models/Domain/Trip.swift"
       provides: "Day derivation methods"
       contains: "func dayNumber(for date: Date) -> Int"
-  key_links:
-    - from: "SortOrderProvider"
-      to: "ItineraryItem.sortOrder"
-      via: "Utilities compute values assigned to sortOrder property"
-      pattern: "sortOrder.*=.*SortOrderProvider"
+  key_links: []
 ---
 
 <objective>
diff --git a/.planning/phases/01-semantic-position-model/01-02-PLAN.md b/.planning/phases/01-semantic-position-model/01-02-PLAN.md
index b972b48..410b11a 100644
--- a/.planning/phases/01-semantic-position-model/01-02-PLAN.md
+++ b/.planning/phases/01-semantic-position-model/01-02-PLAN.md
@@ -15,6 +15,7 @@ must_haves:
     - "Moving travel segment to different day updates its day property"
     - "Inserting between two items gets sortOrder between their values (e.g., 1.0 and 2.0 -> 1.5)"
     - "Games remain fixed at their schedule-determined positions"
+    - "Custom items can be placed at any sortOrder value (negative, zero, positive)"
   artifacts:
     - path: "SportsTimeTests/SortOrderProviderTests.swift"
       provides: "Unit tests for SortOrderProvider"
@@ -115,7 +116,7 @@ xcodebuild -project SportsTime.xcodeproj -scheme SportsTime -destination 'platfo
   <action>
 Create a new test file `SemanticPositionPersistenceTests.swift` with integration tests for semantic position persistence.
 
-These tests verify PERS-01, PERS-02, PERS-03 requirements.
+These tests verify PERS-01, PERS-02, PERS-03, and DATA-04 requirements.
 
 Test cases to include:
 
@@ -137,7 +138,10 @@ Test cases to include:
 **Game immutability (DATA-03):**
 - `test_gameItem_sortOrderDerivedFromTime`: Create game item for 7pm game, verify sortOrder is ~1240.0 (100 + 19*60)
 
-Use in-memory SwiftData ModelContainer for tests:
+**Custom item flexibility (DATA-04):**
+- `test_customItem_canBePlacedAtAnyPosition`: Create custom items with sortOrder values at negative (-5.0, before all games), between games (500.0), and after all games (2000.0). Verify all three persist correctly and can coexist on the same day sorted correctly.
+
+Use in-memory SwiftData ModelContainer for tests. Note: LocalItineraryItem is standalone with no relationships - it can be registered alone:
 ```swift
 let config = ModelConfiguration(isStoredInMemoryOnly: true)
 let container = try ModelContainer(for: LocalItineraryItem.self, configurations: config)
@@ -151,7 +155,7 @@ Tests compile and pass:
 xcodebuild -project SportsTime.xcodeproj -scheme SportsTime -destination 'platform=iOS Simulator,name=iPhone 17,OS=26.2' -only-testing:SportsTimeTests/SemanticPositionPersistenceTests test 2>&1 | grep -E "(Test Case|passed|failed)"
 ```
   </verify>
-  <done>SemanticPositionPersistenceTests.swift exists with 8+ test cases, all tests pass</done>
+  <done>SemanticPositionPersistenceTests.swift exists with 9+ test cases, all tests pass</done>
 </task>
 
 <task type="auto">
@@ -178,17 +182,18 @@ Look for "** TEST SUCCEEDED **" at the end.
 
 <verification>
 1. SortOrderProviderTests.swift exists with 16+ test methods covering all SortOrderProvider functions
-2. SemanticPositionPersistenceTests.swift exists with 8+ test methods covering persistence requirements
+2. SemanticPositionPersistenceTests.swift exists with 9+ test methods covering persistence requirements
 3. All tests pass when run individually and as part of full suite
 4. Tests verify the success criteria from ROADMAP.md Phase 1:
    - Position survives reload (tested via encode/decode and SwiftData)
    - Travel day update works (tested via day property mutation)
    - Midpoint insertion works (tested via 50-iteration precision test)
    - Games use time-based sortOrder (tested via initialSortOrder)
+   - Custom items can be placed anywhere (tested via negative/between/after positions)
 </verification>
 
 <success_criteria>
-- 24+ new test cases across 2 test files
+- 25+ new test cases across 2 test files
 - All tests pass
 - Tests directly verify Phase 1 requirements DATA-01 through DATA-05 and PERS-01 through PERS-03
 - No regression in existing tests