Vincent, 

Imagine I have a Python module, typically hosted on PyPI and depending 
> on SageMath, that provides documentation in some form (e.g. a pdf file, 
> a sphinx repo, etc). 
>
> 1) When a user performs `sage -pip install X`, should the documentation 
>     be compiled and installed? 
>

I can tell you what we do with SnapPy, which has both Sphinx-generated docs 
and some PDF files. When building the sdist tarballs and wheels for posting 
on PyPI, we use Sphinx to compile the docs into HTML and then put the 
resulting HTML files as well as a few random PDFs into the Python package 
as "package data".   There are convenience functions such as 
"spherogram.pdf_docs()" which open the docs in a webrowser or pdfviewer as 
appropriate. As we support vanilla Python as well as SageMath, we can't 
assume that Sphinx is installed.

Best,

Nathan

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