Hubot VS mkdocs-material

2020 - https://github.com/hubotio/hubot/issues/1541 is opened to ask what the plans are

Hubot is kind of old (at least in software terms!), but I’m amazed at how few people know about the ChatOps model. From 10000 thousand feet perspective, it’s just automation through your go-to chat software (discord, slack, rocketchat, mattermost, etc.), and Hubot paved the way to other similar tools. Maybe it’s less relevant today, but I find an interesting concept nonetheless (I love automation in any form it can take) that can solve a few issues, especially for less technical people.

TIL that GitHub are still using Hubot (or at least an account in its name) ... to process DMCA submissions!

Hubot (the framework) has seen little to no maintenance activity from GitHub since a few years back - I'd love to see something from GitHub for how the project could continue.

https://github.com/hubotio/hubot/issues/1541

https://hubot.github.com/ ?

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.