IPod 5 won't sync, old songs "broken"

After importing a CD into my iTunes library, I tried to sync my iPod 5 and after the sync was finished none of the songs appeared on my iPod, so I tried again. When I sync my iPod, as it goes through the tracks it's syncing, it lists 256 tracks that I already have on my iPod... I've updated iTunes, renamed "SyncServices" to "OldSyncServices", and restarted my PC way too many times. The songs haven't appeared on my iPod and have a dotted ring next to the checks when I view the songs under my iPod touch. Since trying to sync it earlier, a bunch of the songs that are already on my iPod refuse to play and get skipped when I shuffle, and then in the songs list they're greyed out and have a square inside a ring next to them. Help?

Maybe:
Re: What does the gray dotted circle in iTunes mean?
What does the gray dotted circle in iTunes mean?
what does the dotted circle mean?
or maybe:
SOLUTION: Some Music Won't Play After Upgrading Your iPhone To iOS7
Red square in red circle cannot play songs
My iPod isn't playing certain songs. Help?

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