I too have tried every option listed above, as well as every option listed on the Apple support site (and I mean every option)and still no luck. Two things that changed around the time this started happening (can't be sure of sequence of events), 1) installed ITunes 10 (actual version is 10.1.1.4), 2) Installed AirPort Extreme (to send music wirelessly to stereo reciever). Not sure if either of these things are the cause, but are suspects because they were changes about the time it started happening. Also of note, I have no errors synching my older iPod classic(20GB)and no errors synching my iPad, just having the errors with BOTH of my iPod 2nd generation Nanos. Very frustrating.