IPod sync failed. Disconnect and reconnect, then try again.

Over the past month or two, I have gotten this message quite frequently with my iPod. It usually happens after I sync my iPod once, leave it hooked up to my iMac for charging, and then try to sync again (sometimes not even more than a few minutes later). I also often have trouble getting my computer to recognize the iPod (or getting my iPod to recognize that it's supposed to start syncing) without having to disconnect and reconnect it and shake the USB cord around a few times.
I had a little bit of this problem with my iPod 5G and XP PC, though no "iPod sync failed" messages ever. This is a new iPod classic and an iMac. What's going on?
Does anyone else have this happen to them?

I'd been having this same issue and kept trying all the suggestions on the forums to no avail. Then I just disabled "Enable Disk Use", which required me to first disable "Manually manage music & videos". I unchecked all of my music, videos, podcasts and photos, applied the settings, then chose which media I wanted in my iPod. I synced successfully and even cleared it out completely a couple of times to re-sync. No issues anymore.

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