Brett Cannon reviews IronPython in Action
Brett Cannon is one of the core Python developers, and despite not developing on Windows he has a keen interest in alternative implementations of Python and has reviewed IronPython in Action:
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To the point: if you need to program for Windows and you want to use Python, you should get IronPython in Action. The book does a good job of walking you through examples covering all the major APIs and tools a Windows programmer will end up using for whatever project they are working on.
I actually read this book while I ate breakfast most mornings. Now that's nothing special, but considering I actually continued to read/skim this book even though I have not actively used a Windows box since 2001 should tell you something. This book is clearly written, and does a good job to point out gotchas you might run into through example. But it also does a good job of not overloading you with extraneous info that you could get from other reference sources (every computer book should have something like Appendix C that is nothing more than a list of URLs for reference material). And as an added perk the authors try to be humorous when possible and are even willing to poke fun at Windows.