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.