[meonkeys]

I wouldn't use Markdown for that.

You're right to start with your requirements. Try to get detailed, like the list @WA wrote out, then match it up with appropriate tech.

I wrote a technical book and I also wanted multiple decent-looking outputs. In my case: HTML, EPUB/mobi, screen and print PDFs. I was struggling with Markdown+pandoc+custom scripts/styles, so I switched to Asciidoc. I wrote about that process here: https://adammonsen.com/post/2122/

Most of the formats came out satisfactory, but there were some gotchas. https://github.com/meonkeys/shb/#%EF%B8%8F-book-formats lists some, and https://github.com/meonkeys/shb/blob/main/issues.adoc has more. Translating from English to German went OK with asciidoc, but it might have been better with docbook and standard translation tools for working with .po files.

Here are two examples where the author used Markdown and the result was beautiful and successful (although layout for printed editions were done with extra/other tooling): http://gameprogrammingpatterns.com , http://www.craftinginterpreters.com . I'm curious if Bob would/will use Markdown for his next book. My process is different than Bob's... I didn't need literate code and I didn't want to do _any_ layout/pre/post-processing, even for print. Asciidoctor worked for this, although there were some compromises (see my links above). Print-ready layout is a lot of work, however you do it.

Is this your first book? Do you have a publisher? Will it be printed on paper? Do you have a developmental editor / proofreader / etc? Do you have a plan for what you'll do after you publish e.g. talks/promos/tour?

Contact me if you want to chat. I'm happy to share my war stories. And good luck!