I have a 400 song playlist that doesn't seem to work right. It only plays a certain alphabetical range of artists. I downloaded the optional media update also.
I used to use it, i hooked it up via the USB. I found it very slow to first read the songs on the ipod. I dont remember if it reads playlists and like you said, just the articst lists which is kinda pointless
Does it bomb out on the same song everytime? Maybe there is some bad metadata on the track - weird/foreign characters, something like that? Or bad MP3 file?