(As a result of the discussion at http://psf.upfronthosting.co.za/roundup/meta/issue605, I started to re-triage all easy issues.)

I don't think this is a suitable task for new contributors. It requires a) good HTML and CSS knowledge b) familiarity with pydoc API c) possibly design of a new API to finish this task.

There are also some key points that needs to be discussed:

* The current API ties to the dated HTML output and we may not need some of the members in the new format (look at the signature of HTMLDoc.section() for example) Also, I know HTMLDoc is not a public API, but I saw a number of HTMLDoc subclasses in GitHub (even I did it myself in my own projects) so there is a risk of breaking working applications. My suggestion is to keep the old API as-is and create a new one with new output.

* The another question is that do we need HTMLDoc in 2016? Sphinx, sphinx-autodoc and readthedocs.org doing an amazing job and it might be better to refer people to alternative solutions (like we did for requests) See also https://mail.python.org/mailman/private/core-mentorship/2016-August/003622.html for a discussion about this subject.