Milestone

/aiagentminder:milestone - Project Health Assessment

Run a milestone health check to assess whether the project is on track. This is the "project standup" that solo developers don't have — a periodic review of scope, progress, complexity, and known debt.

Run this at sprint boundaries, at phase transitions, or any time you want a clear picture of where the project stands.

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Step 1: Gather Context

Read the following:

1. docs/strategy-roadmap.md — current phase, MVP features, out-of-scope items, phase timeline
2. DECISIONS.md — original stack and architecture decisions; also read the ## Known Debt section if present
3. SPRINT.md — current sprint status (if active); archived sprint lines for sprint sizing data
4. Use TaskList to get current task states
5. Recent git log: git log --oneline -20 — what has been merged recently
6. File count and largest files:

   # Cross-platform file count (excluding .git)
   find . -type f -not -path './.git/*' | wc -l
   # Largest source files
   find . -name "*.ts" -o -name "*.js" -o -name "*.py" -o -name "*.go" -o -name "*.rs" | xargs wc -l 2>/dev/null | sort -rn | head -5
   

   (adjust extensions for the project stack; on Windows use Get-ChildItem -Recurse -File | Measure-Object)
7. Dependencies: read package.json, pyproject.toml, go.mod, Cargo.toml, or equivalent

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Step 2: Assess Each Dimension

A. Phase Progress

• Which phase is declared in the roadmap?
• What MVP features are complete (have merged PRs), in progress, or not started?
• Is there non-MVP work that was done while MVP features remain unstarted? (scope drift signal)
• What percentage of Phase 1 features are done?

B. Timeline Health

• What is the declared target date or phase duration from the roadmap?
• Based on the pace of recent merged work, is the project on track?
• Are there open blockers or unresolved questions that threaten the timeline?

C. Scope Drift

• Were any features added to the sprint or codebase that aren't in the roadmap?
• Did any approved issue expand significantly beyond its original scope?
• Check SPRINT.md scope additions if present.

D. Dependency Health

• How many direct dependencies does the project have now vs what was planned?
• Were any dependencies added that weren't in the original stack decision?
• Are there any dependencies that significantly expand the project's surface area?

E. Complexity Budget

Assess whether codebase complexity is proportional to the current phase:

Phase thresholds:

• Phase 1 (prototype/MVP): <50 source files, no single file >300 lines
• Phase 2 (active development): <150 source files, no single file >500 lines
• Phase 3+: growth expected — flag files >800 lines as decomposition candidates

From the data gathered in Step 1:

• Total file count vs phase threshold
• Top 3 largest source files by line count
• Dependency count trend (vs prior sprint if archived sprint data is available)

Flag any file exceeding the phase threshold.

F. Known Debt

Read the ## Known Debt section in DECISIONS.md (if present):

• How many open debt items are logged?
• Which is oldest? Which has the highest stated impact?
• Are any items more than 2 sprints old without a resolution plan?

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Step 3: Present the Health Report

Milestone Health Check — S{sprint_number} / Phase {n}
Date: {today}

Phase Progress:    {X}/{total} MVP features complete ({%})
Timeline:          [On track / At risk / Behind — one sentence why]
Scope Drift:       [None detected / {description of drift}]
Dependency count:  {n} direct ({+/-delta from last sprint if known})
  New this sprint: {list any added, or "none"}
Complexity Budget: [Healthy / Watch / Concern]
  File count:      {n} ({threshold for this phase})
  Largest files:   {file}: {lines} lines, {file}: {lines} lines, {file}: {lines} lines
Known Debt:        {n} items  [{oldest date} — {highest-impact description}]

Recommendations:
- [Actionable item if any concern raised]
- [Or: "No actions needed — project health looks good."]

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Step 4: Flag Hard Issues

If any of the following are true, surface them explicitly before proceeding:

• MVP features unstarted while non-MVP work was done — "Scope drift detected: [feature] was built but [MVP item] is still not started. Recommend pausing non-MVP work until MVP is complete."
• Phase deadline at risk — "At current pace, Phase 1 will complete in ~{N} weeks. Target was {date}. Consider reducing sprint scope."
• File count exceeds phase threshold — "File count is {n}, above the Phase {x} threshold of {limit}. Consider whether all files are necessary or if the project structure needs consolidation."
• Large files that should be decomposed — "{file} is {N} lines, exceeding the Phase {x} limit of {limit}. Consider splitting before complexity increases further."
• Surprise dependencies — "{package} was added but wasn't in the original stack plan. Was this intentional? If so, log it in DECISIONS.md."
• Stale debt items — "{n} debt items are more than 2 sprints old. Review whether they still apply or schedule resolution."