"Songs on iPod 'jerm' cannot be updated because all of the playlists..."

I recently bought a 1GB iPod Nano from a dude on craigslist and I updated it once, but when I try to update it now a message comes up that reads:
"Songs on iPod 'jerm' cannot be updated because all of the playlists selected for updating no longer exist."
Also, when I updated it yesterday, it said that the iPod didn't have room for all of the songs on my iTunes...but I only have like 75 regular-length songs on there and the 1GB is supposed to hold 240. Anyone know what's up with that?
After it informed me of this last thing, it made me a playlist of a "selection" of songs from the iTunes and updated it with those.
I deleted that playlist today...may that be related to my first question?
All of this doesn't make sense. Can anyone shed a little light on the subject?
Thanks
Sony VAIO   Windows XP  

I had this problem with my 4GB iPod nano and I tried everything that you said to try. I did accidentally delete the iPod Selection playlist and I tried to make a new smart playlist. When I did this I got an error message that said "The smart playlist contains one or more conditions which are empty of conflict with one another. This will result in never matching any item. Are you sure you want to save this playlist?" I tried to upload an old library onto my iTunes and it was successful, however, my iPod would still not sync. Do you know what i can do to fix this?
thank you.

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