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iPod Classic can not cync due to 3 different warnings. what to do?

Hi there.

I have serious issues with my iPod Classic. I accidentally reset my iPod and now when I start to sync, it freezes after about 600 songs. Then I get a warning that he cannot sync due to a file with the exact name that already exists. After trying again and again, i sometimes get other warnings about an unknown error (-50) and (-53). My iTunes is just updated and my Ipod Nano 4th generation doesn't have any problem.

Any tips? I tried many of the already existing solutions but so far no luck...