Anybody have any advice for writing extensive documentation that outputs to multiple HTML pages? I've been fighting with docbook related stuff and I'm coming to the conclusion that it is a hyper-complex ill-maintained stack of shit.

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I like MKDocs with Material Theme.

Not sure what your exact needs are, but I love Nextra. Uses markdown but supports advanced stuff with react.

https://nextra.site/

This is a popular tool in the Rust community I hear very good things about:

https://github.com/rust-lang/mdBook

I have a love/hate relationship with Markdown Jekyll and Liquid for producing HTML from docs

Not sure if it does multiple pages but I’ve been pretty happy with ascii doc https://asciidoc.org/