I've said good things about XPlay in the past, but boy - if you get Windows bit rot, bad things happen.
When I was experimenting with the COM interface to iTunes, I had to uninstall/reinstall. I probably could have just upgraded XPlay - there's a patch that says it updates to iTunes 7.x. Not noticing, I went to what I figured was the safest route: uninstall, reinstall, update.
Oh boy. I had to reboot after each step. Would it be too hard to have the installer kill and restart the application? Sheesh.
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XPlay, iPod