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Backfill CHANGELOG and require [Unreleased] updates in contributor PRs #45

Description

@rosspeili

Problem Statement

CHANGELOG.md exists but only documents its own creation. Merged work since settings YAML (#26/#28), slim deps (#35), Ollama preflight (#36/#43), and related fixes is not recorded. Skillware treats the changelog as a contributor contract: user-visible PRs add lines under [Unreleased]; maintainers cut version headers at release time.

Without this, users and contributors cannot see what changed between clones, and pre-release history is lost when we publish to PyPI.

Proposed Solution

  1. Expand CHANGELOG.md following Keep a Changelog with a retrospective [Unreleased] or initial 0.1.0 section covering merged milestones (settings YAML, persona/config work, dependency split, Ollama preflight, --skip-preflight, test additions). Reference issue/PR numbers where known.

  2. Update CONTRIBUTING.md and README changelog blurb to match Skillware policy:

    • Contributors add user-visible entries under [Unreleased] in the same PR (Added / Changed / Fixed / Removed).
    • Maintainers rename [Unreleased] to a version + date when cutting a PyPI/GitHub release.
    • Do not bump version numbers in routine PRs.
  3. Add a short "Changelog" subsection to docs/TESTING.md or a one-line pointer in PR review checklist (see separate PR-template issue if filed later).

Acceptance criteria

  • CHANGELOG.md lists notable merged work through current main
  • CONTRIBUTING.md states when changelog updates are required vs optional
  • README still links to CHANGELOG.md

Alternatives Considered

  • GitHub Releases only — rejected; no in-repo history for agents and offline readers.
  • Wait until first PyPI tag — rejected; we are already shipping features on main; backlog is growing.
  • Automated changelog from commits — defer; commit messages are inconsistent; manual Keep a Changelog is enough for now.

Priority

Medium 🟡

Additional Context

Skillware reference: root CHANGELOG.md + contributor note in CONTRIBUTING.md ("Contributors add user-facing entries under [Unreleased] in the same PR").

Related: original CHANGELOG request (#10, merged via #41). This issue is the follow-up to populate content and enforce process.

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