Error message "The iPOD "abc's iPOD Touch" cannot be synched ...

I get this error message when I try and synch my iPOD Touch with iTunes 10.5.3. I have OSX 10.6.8 on my iMAC.
Error message "The iPOD "abc's iPOD Touch" cannot be synched. The required file cannot be found."
I have this model: APPLE iPod touch, 8.0GB, Generation 3 (MC086FD).
I have been to the local apple store 5 times and they have no idea how to fix this.
My wife and I have lost all our personal contact database.
Any cleaver ideas?
T & A

Deleting the iPod Photo Cache folder(s) usually resolve your error.  There can bemore than one folder. For it location:
iTunes: Understanding the iPod Photo Cache folder

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