I've been looking all over to figure this out. Nobody seems to have a straightforward way of doing this. I have switched from an iMac to a PC and am trying to transfer over all of my iTunes stuff onto the new system. I can manage to get my music and some of my movies (the most recently added ones have audio but no video) onto the PC without a problem, but I can't get my playlists or anything back over here as well. If it helps to know I have both an iPod Touch and an iPod Classic. PLEASE, somebody give me a real answer on how to do this. It shouldn't be so complicated.