With the iPod problem, can OS X read a windows formatted iPod just as a hard drive without using iTunes? I backed up all of my songs by putting them on the iPod HD as well as the normal iPod sync method. So, I'm able to just get them off as both a music file and a file that plays on the iPod. Would that be a viable way to have them transfer their music? Just save them as files to the iPod, transfer them to the iMac as files without using iTunes. Then, you just re-format your iPod in OS X form, and re-sync.