mdBook VS mkdocs-material

I'm responsible for a number of Java products. I try to provide high-quality Javadoc for all public library interfaces, library user's guides where appropriate, and development guides for applications. The latter two take the form of MDBook documents (https://rust-lang.github.io/mdBook/), with the document source living in the GitHub repo so that it's tied to the particular software release in a natural way.

My org has used mdBook: https://rust-lang.github.io/mdBook/ (That link is itself a rendered mdBook, so that'll give you an idea of the feature set.)

(While it's definitely a Rust "thing", if you just have a set of .md files, all you need is a "SUMMARY.md" (which contains the ToC) and a small config file; i.e., you don't have to have any Rust code to use it, and it works fine without. We document a large, mostly non-Rust codebase with it.)

If you want the lowest friction, open source, easily extensible Markdown to Web, Kindle, PDF, etc. tool, highly recommend mdBook: https://github.com/rust-lang/mdBook it’s written in Rust, but you don’t have to know any Rust to use it. And then wing is all CSS; for which there are many good (free) themes.

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.