Mike, I don't know if this has already been suggested, but you can emulate the whole Windows XP (or any other brand of WIndows) environment with a proprietary package called VMware. Unfortunately, it does a cost a small sum, ~$200. I actually bought it recently thinking that it would be fun to emulate a Windows XP box set up in its default state (naked to the world) and watch the viruses and worms wiggle their way in. I never got around to doing this but I thought it would be a fun and secure way to learn about Windows vulnerabilities. I can't tell you how well it works, as I have yet to install it. There may well be other Debian users out there who have used it and may be able to tell you how well it works.
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