Error iPod Photo won't update

I have 2600 songs in my library, but my iPod photo will only update about 1500. Then I get an error -XX Unable to update Cali's iPod an error occurred. I have 60GB so I know it is not a capacity issue. I tried the tips from Apple (deleting the photo directory) and completely re-formatting my iPod 3 times.
To make things worse. My library keeps getting corrupt and I have to import my CDs over and over again. The new thing is that all the files are being renamed to four letter files randomly. I have spent literally days on this. Can someone please help me? I never had this issue with my 20GB regular iPod. Could that be it?
Please help,
Cali

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