When replacing Pico, decide whether the flat-file model is a requirement or merely the current implementation. Compare Markdown compatibility, front matter, routing, themes, plugins, multilingual content, asset handling, caching, search, preview, and deployment. Test the existing content tree and custom Twig behavior in a prototype. A database-backed CMS may add editorial features while increasing operations and migration complexity. Inventory URLs, redirects, metadata, templates, and build hooks, and keep the old site deployable until parity is proven.