Won't Sync: no playlists exist catch 22

I've seen a lot of posts about this around the web and all of the solutions seem to be "change the iPod preferences when it's plugged in" - here's my new angle:
(Just upgraded to latest version of iTunes this morning by the way)
I plug in the nano, it says "can't sync, etc etc, all of the playlists selected no longer exist". It then pauses and the iPod screen returns to the main menu and iTunes has disconnected it. I'm free to change the settings, but when I click apply it can't find the nano because it's already ejected it, and throws an error, consequently I'm unable to actually change the settings about WHICH playlist(s) should be synced - does anyone know how I can get around this? I'm happy to start hacking config files if it'll help!

Did you have it set to sync to specific playlists which you subsequently deleted? If so, maybe you could try recreating the playlists (assuming you know the names). I don't know if it would work if it was just a playlist with the same name or if it would have to contain the same tracks.

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