HT3798 Ipod Classic will not sync with windows 8 and newest itunes

I have ipod classic, 160gb, with new computer with Windows 8 and latest version of Itunes - came from xp and previous version of itunes - and never had a syncing problem. 
All my songs are in new itunes on new computer, however ipod will not sync.  Have received -50, and duplicate file name - I restored and it will go so far and then freeze.  Or  I get -53.  Have tried lots of suggestions discovered on pages like these... but none have worked.  I do see there is a problem with classic and new itunes - does anyone have any solutions??
Thanks.....

Well I finally figured out the problem, not thanks to anyone from Apple for that matter. You would asume this problem has happened before and is still happening. The problem was I couldn't copy certain songs anymore from iTunes to my iPod Classic. When trying to copy certain songs I got an error.
If you have this problem it means your song file is corrupted. You can simply check this by trying to copy it from your hard drive to an external hard drive. Here you will also get an error message.
This means you need to replace all the corrupted files by a back up on your hard drive or download it again. I did this and now everything works fine.
Hope this will solve a lot of problems.

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