So. Armed with my new favorite IDE -- PyDev, the first thing I'm starting to look for is a strategy for unit testing Python. Since I'm starting afresh, I'm planning to write tests to lay out my objectives, then learn how to create the functionality for the tests.
I'm not trying to be blinded too much by the way I usually work, but my expectation is that I will be able to find a unit testing framework that can be integrated into PyDev (or Eclipse, as the case may be). Then I can write tests that will live "alongside" my classes and I can run the tests programmatically.
We'll see.