I have about 39 gigs of mp3's and a 40 gig iPod, which means I cant fit all my mp3s onto my iPod. What option should I choose? If I choose to let iTunes put what it thinks should be on there, then I get only one playlist (a playlist with every song I own) and no other playlists and cant seem to find a way to add my original playlists. However, if I choose to update the playlists only and not let iTunes decide, then I get ONLY the playlists and no other artists. Is there a way to get the best of both worlds (like by having iTunes not upload songs I havent listened to in a while)? If not, what would you choose?