IPod Won't Update with New Playlists and Audio Only

My iPod will not update new playlists that have been created or add any audio files from iTunes. Videos come over just fine. Powerbook 12" G4 with 10.4.4, iTunes 6.0.2. Latest iPod software, 0106, deleted the old iPod updates. Also, did a hard reset on the iPod.
Under my administrator test login, playlists and songs come over fine, but I can't seem to get it to work in my regular account. Any idea what do do without reformatting my hard drive and reloading software?

I also just started having this trouble on my 6 month old nano. I have it set to automatically update selected playlists only. I update the songs in those playlists in itunes, then I connect my ipod to my PC. The ipod and itunes say it is updating, but when done the same old songs are on the playlists in the ipod. Itunes does show the correct playlists with the update songs, they just don't seem be updating on the ipod, even though there seems to be a good connection and the ipod says it is updating when plugged into the PC. Any thoughts?

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