Trouble updating my ipod

I have a 20G ipod and recently went over this limit in itunes. When I updated my ipod a playlist was created called, I belive, 'ipod selection'. I edited my itunes down to less then 20G and deleted the created playlist. When I tried updating my ipod the following message appeared:
'Songs on the iPod ''IPOD'' cannot be updated because all of the playlists selected for updating no longer exist.'
This wiped all songs from my ipod. How do I update my ipod?

My preferences are already set to sync music - all songs and playlists. After I sync my iPod I will have all of my music, it is just that after a period of non-use, the songs that were purchased thru iTunes no longer play. They will show up in all directories, but the iPod will skip past those songs when it comes to them. This does not affect any songs I had downloaded from a CD though.

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