Trouble syncing iTunes files with iPod.  Help!

Hi. Newbie, so be gentle.
I have a lot of songs on my computer. Sometime in the past couple of months, something prevented me from updating certain song files (and the files would vary). What would happen is the iPod would go through the syncing process and get hung up on one song (visible in the the status bar in iTunes). After it gets hung up, the syncing process would stop and I'd get the "OK to disconnect" message, but the file never showed up. On occasion, deleting the song and attempting to resync would make the iPod usuable again (and then I'd just have to reload the song and try again--sometimes that would work, other times it wouldn't).
After numerous problems with this, I talked to a rep at my local Apple store, who suggested that restoring my iPod would be the best solution. So I did. After taking multiple attempts to restore, I finally got the iPod blanked out. But now when it tries syncing to get all of my songs back, it again gets hung up on one song and stops attempting eventually. So from almost 5000 songs on my iPod, I've gone to 14.
Please help! I don't want to buy another iPod (especially because I don't know whether this is a hardware issue with my iPod or a softeware issue with my iPod or iTunes--buying another iPod isn't a guarantee that the same thing won't happen). Hoe else can I troubleshoot this issue?

Sad to say, but I think you have some corrupted music files.
Those are the worst to filter through....
My iPod was doing something similar. Wouldn't update. I finally found the bad file. It wouldn't play in WMP or winamp either, so it wasn't just iTunes being funky.
Luckily mine were like, 5 bad files in a row. Otherwise it takes forever to isolate which ones are causing it.
You could send feedback, I guess...if iTunes finds a bad file, then skip it, instead of shutting down the entire sync process. Maybe if enough of us send this suggestion, it will be implemented.

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