chore: add handoff system for long-running sessions

Add bootstrap.sh and checkpoint files for 2-hour handoff cycles:
- CONTINUE.md - Quick start guide
- CHECKPOINT.md - Current state (updated by Kimi)
- TODO.md - Remaining tasks
- bootstrap.sh - One-command status check

.handoff/CHECKPOINT.md

@@ -0,0 +1,65 @@
+# Kimi Checkpoint - Updated 2026-02-22 18:50 EST
+
+## Session Info
+- **Duration:** 4 hours
+- **Commits:** 1 (f0aa435)
+- **PR:** #18 ready for review
+
+## Current State
+
+### Branch
+```
+kimi/sprint-v2-swarm-tools-serve → origin/kimi/sprint-v2-swarm-tools-serve
+```
+
+### Last Commit
+```
+f0aa435 feat: swarm E2E, MCP tools, timmy-serve L402, tests, notifications
+```
+
+### Test Status
+```
+436 passed, 0 warnings
+```
+
+## What Was Done
+
+1. ✅ Auto-spawn persona agents (Echo, Forge, Seer) on startup
+2. ✅ WebSocket broadcasts for real-time UI
+3. ✅ MCP tools integration (search, file, shell, Python)
+4. ✅ /tools dashboard page
+5. ✅ Real timmy-serve with L402 middleware
+6. ✅ Browser push notifications
+7. ✅ test_docker_agent.py (9 tests)
+8. ✅ test_swarm_integration_full.py (18 tests)
+9. ✅ Fixed all pytest warnings (16 → 0)
+
+## Next Task (When You Return)
+
+**WAITING FOR PR REVIEW**
+
+User is reviewing PR #18. No new work until merged or feedback received.
+
+### Options:
+1. If PR merged: Start new feature from TODO.md P1 list
+2. If PR feedback: Address review comments
+3. If asked: Work on specific new task
+
+## Context Files
+
+- `.handoff/TODO.md` - Full task list
+- `git log --oneline -10` - Recent history
+- PR: https://github.com/AlexanderWhitestone/Timmy-time-dashboard/pull/18
+
+## Quick Commands
+
+```bash
+# Check current state
+git status && git log --oneline -3 && make test
+
+# Switch to PR branch
+git checkout kimi/sprint-v2-swarm-tools-serve
+
+# See what changed
+git diff main --stat
+```

.handoff/CONTINUE.md

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+# Kimi Handoff - Continue Work
+
+## Quick Start
+
+```bash
+cd /Users/apayne/Timmy-time-dashboard && cat .handoff/CHECKPOINT.md
+```
+
+Then paste this prompt to Kimi:
+
+```
+Continue work from checkpoint. Read .handoff/CHECKPOINT.md and execute NEXT TASK.
+```
+
+---
+
+## Current Status
+
+**Last Commit:** (will be updated)
+**Branch:** (will be updated)
+**Next Task:** (will be updated)
+**Test Status:** (will be updated)
+
+## Files to Read
+
+1. `.handoff/CHECKPOINT.md` - Full context
+2. `.handoff/TODO.md` - Remaining tasks
+3. `git log --oneline -5` - Recent commits
+
+## Emergency Commands
+
+```bash
+# If stuck, reset to last known good state
+git stash && git checkout main && git pull
+
+# Verify tests pass
+make test
+
+# See what was recently done
+git diff HEAD~1 --name-only
+```

.handoff/TODO.md

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+# Sprint v2.0.0 - Remaining Tasks
+
+## ✅ Completed
+- [x] Swarm E2E (auto-spawn, WebSocket broadcasts)
+- [x] MCP Tools (search, file, shell, Python)
+- [x] timmy-serve L402 implementation
+- [x] Browser notifications
+- [x] Test coverage (436 tests, 0 warnings)
+- [x] PR #18 created
+
+## 🔄 Next Up (Priority Order)
+
+### P0 - Critical
+- [ ] Review PR #18 feedback and merge
+- [ ] Deploy to staging and verify
+
+### P1 - Features
+- [ ] SQLite connection pooling (retry with proper test isolation)
+- [ ] Add more persona agents (Mace, Helm, Quill)
+- [ ] Task result caching
+- [ ] Agent-to-agent messaging
+
+### P2 - Polish
+- [ ] Dark mode toggle
+- [ ] Mobile app improvements
+- [ ] Performance metrics dashboard
+
+## 📝 Notes
+
+- SQLite pooling was reverted - need different approach
+- All tests passing - maintain 0 warning policy
+- Docker swarm mode working - test with `make docker-up`

.handoff/bootstrap.sh

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+#!/bin/bash
+# Kimi Bootstrap - Run this to continue work
+
+echo "=== Kimi Handoff Bootstrap ==="
+echo ""
+
+cd /Users/apayne/Timmy-time-dashboard
+
+echo "📋 Current Checkpoint:"
+cat .handoff/CHECKPOINT.md | head -30
+echo ""
+echo "---"
+echo ""
+
+echo "🔧 Git Status:"
+git status --short
+echo ""
+
+echo "📝 Recent Commits:"
+git log --oneline -3
+echo ""
+
+echo "✅ Test Status:"
+source .venv/bin/activate && make test 2>&1 | tail -3
+echo ""
+
+echo "🎯 Next Task (from TODO.md):"
+grep "\[ \]" .handoff/TODO.md | head -5
+echo ""
+
+echo "================================"
+echo "To continue, paste this to Kimi:"
+echo ""
+echo "  Continue from checkpoint. Read .handoff/CHECKPOINT.md"
+echo ""