On the other hand, I wonder if such problem/solution pairs should go in the FAQ list rather than the howto, perhaps with a pointer to the howto for those wanting more general information.  Specifically the Python on Windows section in this case.

I realize that you were using it as an example to tease out the concepts needed to reason correctly about a problem, but I think approaching it from the point of view of how the user will reason about it is not optimal.  Instead, write the FAQ answer, and figure out what concepts you need to use to *explain* the problem, that you then feel the desire to further expand upon in the howto for those users who reach for a deeper understanding instead of just an immediate solution.