Syncing my New iPod - Some files do not transfer

I just upgraded from 30GB to 80GB and when I went to sync my new iPod it left out like 5 (of 2550) songs and 40 videos (of 80+). I changed to Manually manage and was able to add the files, however, I wish to keep auto sync on and don't like the idea of manually doing it. I can not see any reason why these files were left out of the sync. It is not an authorization problem as all of my videos were purchased from iTunes Store and half of them were transfered. I only have one iTunes account so it is not multiple authorizations. Can anyone help me with this?
Custom Built   Windows XP Pro  

I was thinking that this was a file type error, but when you manually transfered over media onto your iPod, everything worked fine?
Try keeping the Auto Sync feature on for a while and see if any new media it finds is automatically transfered over.
Hope it helps!

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