Ipod Touch not syncing smartlists?

I’ve had quite a few problems with my playlists ever since upgrading to the iPod touch. The smart lists don’t update once the list has exhausted all the songs. Instead it keeps playing the same list of songs over and over again even though I’ve set the parameters of the list to not play the songs more than once in a one day period. And now I have three smart playlists that are actually quite dumb. Even though I have songs listed in iTunes for those lists when I update my iPod the playlist is empty.

Does anyone know why this is happening and, more importantly, how I can fix it? I’ve got a nine hour drive coming up and I really want those playlists working.