Help - nano driving me crazy

Have the latest edition of iTunes.
When I iniially connect my ipod, it will only upload songs from the library, and creates a new playlist from which it will always upload from. I've tried to get one of my playlists on there, but it simply won't replace anything aready on there. I've tried the follwing:
-Updating the paylist it updates from - says too much is already saved on nano
-deleting everthing on the nano from via itunes - only deletes song list temporarily and everything is still on there when I re-connect
-restoring my nano - will only upload from library again
-resetting my nano - no effect
Any other suggestions?

there won't be because the auto sync music is still there.
Select Manual update.....then in iTunes, select iPod in left hand pane, highlight all the music in the iPod and click, select clear.
Then set music preference to the playlist(s) that you want. Right click iPod to update.

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