iTunes update problem

iTunes 6.0.2 updates all songs on my photo ipod just fine, but on my daughter's new Nano video 30gb it only adds songs that were ripped after I first synched it. I've resynched, updated, consolidated, rebooted, made a playlist with everything in it to no avail. It also will not let me ctrl-a the list and drag it to the ipod, it "not happening" little icon stays when over the Nano. tia