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I took another look at this and found click-man, which is a tool that creates man pages for Click applications. You install the tool and run one command and all your man pages are generated (one per command/subcommand). Interestingly, the docs for the package explain why we shouldn't automate that on build (rather than documenting how to automate it). The short of it is that Python builds are system agnostic while man pages are system specific. Also, if installed in a virtualenv, the manpage should not be installed (a reason they miss).
So if you are building deb/rmp/etc packages, then you can use click-man to generate the man page, It's just one more line in your build script. Or, if you installed MkDocs via pip and want a man page, you can
Therefore, my proposed resolution of this issue is to document how to use click-man in the installation documentation and be done with it.