My iPod Nano recently started skipping some songs here and there. I thought that maybe there was a problem with the music file, but it would play fine on the PC. I had purchased the song in iTunes, so it wasn’t a problem with a rouge file or anything like that. I tried these steps recommended by Apple here.

First I reauthorized my iTunes.

1. In iTunes, choose Deauthorize Computer from the Store menu (your computer needs to be connected to the Internet).
2. In the resulting dialog, enter your Apple ID and password.
3. Click OK.

That didn’t work, so I had to restore my iPod to the factory settings. Finally that did it. It was kind of annoying to have to reload all of my music over again.