My iPod Classic sync keeps failing with iTunes 11.4

Question

My 80GB iPod Classic stopped syncing with iTunes once it'd updated to iTunes 11.4 and then the memory failed (at least I think so as it no longer seems to have any, even though it has no music on it). Assuming this was an issue related to my dying iPod, I purchased a second hand 160GB iPod Classic that has been tested and should be working fine yet when I tried to sync it with my iTunes yesterday it would copy about 8 tracks and then freeze, giving me the spinning beach ball of doom before eventually telling me the sync had failed and giving me the error message -1401 (which I can't find anywhere online). According to iTunes some of the memory has been used up and the iPod says that there is now 7gb less free memory than when I got it but there's still nothing on my iPod. When the iPod is plugged in it says it has zero capacity according to iTunes yet the bar along the bottom shows it has plenty of free space. I've tried restoring it, restarting it, etc but to no avail. Please help!
I currently have iTunes 11.4 and use Mac OS X Mavericks (not quite sure which release currently as I'm at work but it was updated recently) on an iMac from 2009/2010 trying to sync with a 160GB iPod Classic (which currently claims to have 141GB of free memory even though it has no content on it).

Answer 1

You might want to read through this post I recently wrote summarizing what can lead to synchronization problems. My first suggestion would be to determine whether the problem lies with iTunes/your computer or the iPod itself. To that end, if you have a friend with a working iTunes setup (or at the Apple store), I'd see if you can get that machine to at least connect to your iPod and restore it with something... anything. If that works, you know the iPod itself is OK and not corrupted, and you can look at disk diagnostics and such. If that doesn't work, then contact a Genius bar for service.
If the problem is on the iTunes/your computer side, my post cited above should help. I'd suspect the problem is in the underlying Apple media drivers, and I'd move back through the iTunes versions until I find one that works. Note that, at some point, you may no longer be able to read the backed Itunes library (and do back up your libraries). If that happens, you should be able to reimport your music from where it is on disk, but you may lose metadata such as ratings, play counts, and playlists.