Port to modern Python stack (Python 3 + Flask + Fly.io)

[simonbc]

Goal

Port the 2007 Jottit codebase (Python 2, web.py 0.22, Jinja 1, psycopg2 0.6, reCAPTCHA v1) to a modern Python stack and deploy it to Fly.io — as a natural progression of what's here, not a from-scratch rewrite.

Target stack

• Python 3.12, Flask + Blueprints with host_matching=True (subdomain routing day 1)
• SQLAlchemy Core + Alembic
• mistune v3 (markdown) replacing markdown2 1.0
• nh3 (HTML sanitizer) replacing the bespoke sanitize.py
• Cloudflare Turnstile replacing reCAPTCHA v1
• uv + ruff + pyright for tooling
• Deployed to Fly.io (Dockerfile + fly.toml + wildcard cert)

Approach

Incremental — one small PR per step, merged to main continuously. Original 2007 code at app.py, db.py, etc. stays as the starting point; new code lands in a jottit/ package alongside.

Milestones

• M1: Project skeleton (Flask app, blueprints, DB tables)
• M2: Site resolver + index/new-site flow
• M3: Page view + edit + draft
• M4: Auth (sessions, claim, signin, password)
• M5: Admin (settings, design, URL, delete, export)
• M6: History, diff, revert, changes, atom feeds
• M7: Templates port (Jinja 1 → Jinja2)
• M8: Turnstile + Alembic + Dockerfile + fly.toml

Each PR in this effort links back here.

🤖 Tracked with Claude Code