FWIW I almost always use "print" for debugging, and find the use of a real debugger overkill in Python in most of the cases.  People coming from other languages often feel the need of using a debugger because that's what works best with the other languages, but it's not necessarily true for Python.

I'm not sure focusing on pdb is the best idea then.  While it should be mentioned and a quick overview should be presented, a more extensive guide should probably go alongside the pdb doc, or possibly in a pdb-specific howto.

Mentioning unittest and coverage as a way to find errors earlier might also be a good idea (and reply to the "it's easier to debug compiled code because if I do something wrong the compiler gives me an error immediately" argument).

But all this might not be what you had in mind :)
I'm wondering if, for this kind of work, it's better to set up a clone with the document and its outline, in order to allow different persons to work on it before pushing it.  Rietveld works well for corrections, but a clone is better if you actually want to add something (and faster if you want to make corrections).