outline-docker-compose VS mkdocs-material

I recently found this. Never Got to try it, but it seems simple: https://github.com/vicalloy/outline-docker-compose

here is the official website and here is an example compose file.

Material Mk-Docs by Martin Donath works well if you prefer python.

https://squidfunk.github.io/mkdocs-material/

I'm an 'outsider', but from from the outside the Material For MkDocs Project looks like a very well managed open source project.

Martin Donath's project uses a 'sponsorware' release strategy to generate donations.

From my vantage point it seems to be working pretty well.

I just recently went through this decision process. My aim is to write code and math oriented posts so I need good support for nice syntax highlighting (at least colored) and mathjax (preferable) or katex. Substack is the most popular newsletter platform but fails at these two criteria. I love how math and syntax highlighting (plus numerous other features) work in MkDocs Material, which recently added a Blog plugin.

I wanted to combine the best of both: Substack as an amazing email social network, and MkDocs Material’s awesome look. So I’ve gone with using Substack as the core platform which I use to manage subscribers, and use it to post either math/code-free posts or a short teasers pointing to my main blog site on MkDocs Material when I need to show math/code

https://squidfunk.github.io/mkdocs-material/

I've been migrating content to MKDocs (Material) over the last few months, so feel fairly qualified on this subject. It's somewhat limited in terms of navigation, but can probably handle 400-500 pages; you can see how navigation works in the link. Otherwise, it can handle most, if not all, the tasks you've listed.