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FYI... sold my iPod classic for $329 on eBay a little over a year ago. I paid $299 for it 10 years ago. Bought a $40 usb drive... stuck the music on it... and forgot all about the iPod
This. Try the hard reset...it cures most of my issues. But Sync and a loaded iPod just don't play well together...indexing kills it.Did you try resetting the iPod? Did you also try a different usb cable?