iPod touch odd syncing behavior...

2 problems actually:

1. It seems my iPod touch (latest iOS 5.1) keeps syncing the same 33 songs over and over again. I suspect it might be broken ID3 tags for the songs, but how do I find out if that is the case and how do I fix it?

2. One of my iTunes playlists is a smart playlist that keeps track of songsI played in the last 4 days called "Recently Played". It has live updatingturned on, so playing on either my computer or iPod touch will increment the past played attribute. But lately, it has not been syncing properly. What is odd is that in iTunes on my computer, the iPod in the sidebar shows the playlist with all recently played songs correctly on the playlist. But when I fire up my iPod, and pull up that playlist, there are no songs on it at all. iTunes thinks it has synced it properly, but it does not show up on the iPod touch.

I have tried everything to fix these problems including resetting the iPod to factory settings and reinstalling all software, music, etc...and the problem still persists.