MD->HTML->PDF. Just use a browser to render your document. You can make the process a bit more automated by using something like Chrome Headless. I'm sure there's a project out there that does this all in one step from the commandline.
1) I have cmark installed
2) https://github.com/nathanl/.dotfiles/blob/master/bin/md_prev... is a script to render STDIN to HTML and slap the output into the middle of a template that has some basic CSS (https://github.com/nathanl/.dotfiles/blob/master/bin/md_prev...)
3) I write markdown in Vim and use keybindings to say "now output HTML from this buffer" - https://github.com/nathanl/.dotfiles/blob/ede8c98a7897ee07b7...
I like this mainly because it lets me use Vim, which for me is the most efficient tool for wrangling text. I also like avoiding WISYWIG programs that I previously fought with - eg, trying to get Word to understand which bullet points I wanted nested under which other ones was frustrating, but with markdown (and embedded HTML when necessary) I can be 100% explicit.
Sometimes I copy-paste the resulting HTML into Google Docs or elsewhere and do further tweaks, but most of the time it's enough for me as-is.
[0]: https://developer.mozilla.org/en-US/docs/Web/CSS/page-break-...