Error msg when trying to sync new songs to iPod 2nd gen.

I can't get newly downloaded songs to sync to my ipod nano 2nd gen.  They show up & play in iTunes.
I have downloaded latest iTunes software & reset/restored my iPod & continue to get the following message:
Can not sync song. An error has occurred. (+50)
I need a new playlist - help!

Could be a problem with the iPod's hard disk or file storage. Maybe try doing a low level reformat of the iPod's storage using the instructions in this article.
http://www.methodshop.com/gadgets/ipodsupport/erase/
Otherwise, it may be time to start investing in a new one.
B-rock

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