Thanks, I ended up finding one for $20 that worked great... I probably could have done it for free, but it was worth it to be able to get all of his music back into iTunes library and then Erase and Synch so he can update his iPod on this computer.
In case anyone ever has a crash and wants to put all their music back into iTunes.. this was seamless:
MediaWidget - iPod Transfer Software
Website:
Bootstrap Software Development - Makers of MediaWidget for your iPod