Can anyone help me fix my iPod/iTunes problem?

I have an iPod Touch Gen 3 with iOS 5.1.1.  I'm running Windows 8 (which is probably my first problem) and iTunes 11 or whatever the latest one is.  For whatever reason, whenever I add a song from my laptop to my iPod, the song: A) either skips, only plays the first couple of seconds and then goes on to the next song, or doesn't play at all and goes on to the next song, and B) has heavily pixelated and distorted artwork.  I originally thought that it was my old iPod screwing up, which is two years old and semi-broken, so I assumed it was just ready to die.  I've deleted and reinstalled my iTunes, but that didn't help.  I'm going to run a security scan soon to see if there's anything wrong with the iTunes files.  If anyone has had this happen and knows how to fix, or if anyone has an idea to give me a direction to go, please help me out.

Troubleshooting songs that skip
- Unsync all music and resync
- Restore from backup. See:                                 
iOS: How to back up                             
- Restore to factory settings/new iOS device.
If still problem, make an appointment at the Genius Bar of an Apple store since it appears you have a hardware problem.
Apple Retail Store - Genius Bar                       

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