IPod won't update due to playlist error

I've got the 20 Gig scroll wheel iPod that has worked perfectly in the past. I recently updated to the newest iPod software and I'm running the newest version of iTunes.
About a week ago, after updating to the newest version of iTunes, iTunes came up with a message about how I had too much music on my iPod and that it couldn't update the entire song library, and instead offered me the choice of making a "Smart Playlist" to update instead of updating the entire library. I've since pared down my library, and now when I try to update my iPod, it has an error that says the playlists that are supposed to be updated no longer exist. What's worse, every time I change the option from "Update Selected Playlists" to "Update Entire Library" it will neither update nor will it save that configuration.
Any help?

Anne,
Check this out.
Hudgie, "iPod cannot sync because one or more playlist", 11:33pm Oct 9, 2004 CDT

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    Check this out.
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