First Generation iPod Syncing Problem

Hello,
My first generation iPod battery died a while ago, but I use it in a sound dock. I recently decided to change the music on there but when I try to sync it with iTunes, sometimes it says it can't update because the playlists no longer exist and sometimes I just get an error message from Windows saying I have a USB device which is not working properly.
Any thoughts ?
Message was edited by: Steve-Dave

yeah this just started happening to me too for some reason. I figured out how to fix it by reading other posts, you have to right click on the playlist, edit playlist, click + to add another rule, select "playlist" "is" "music". then re-sync. sounds more complicated than it is, but it fixed mine.

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