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Break TODO.md (3,169 lines) into GitHub milestones + issues

#6
Open glennmichael123 opened this 11 days ago ·
11 days ago

Context

TODO.md is 160KB / 3,169 lines tracking 18 phases of work. Today the issue tracker has 0 open and 0 closed issues — all the actual work tracking lives in this single, invisible markdown file.

Consequences:

  • External contributors can't see what's in flight or what's available to pick up
  • No way to discuss / comment on individual items
  • No way to assign / prioritize / close
  • The file is too large to read end-to-end, so it doubles as a graveyard for completed work

Proposal

  • Create GitHub Milestones for each top-level phase (or for the next 3-6 months of phases that are still active)
  • Walk TODO.md and convert unchecked items into individual GitHub Issues, assigned to their milestone
  • For completed items: either delete from TODO or move to CHANGELOG.md (which already exists)
  • Replace TODO.md with a short pointer file: "Active work is tracked in GitHub Issues and grouped by Milestones"
  • Optional: use a single "umbrella" issue per phase that links to its sub-issues, for high-level visibility

Cost vs benefit

  • Mechanical work; can be done incrementally (start with the next phase, leave the rest in TODO.md until you get to them)
  • Pays back the moment the first external contributor lands here looking for "what can I help with"

Could be a good test case for gh issue create --milestone scripted from a TODO parser if the conversion turns out to be tedious manually.

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