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Can a single computer play different songs from the same HD at the same time?
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I think so. Try this:
http://www.musicex.com/mediacenter/
It's still in beta but it's running well enough that you can buy it. Media Center has two "zones" and I'm pretty sure you can play different files in each zone. They just did some sort of update to that feature but since I have no need for the multiple zone feature I am a bit uninformed. I'd suggest you hang out in their forum here:
http://www.musicex.com/cgi-bin/yabb/YaBB.cgi?board=beta.