How do you do it? Do you randomly select the songs to be synced, do you have certain playlists used for syncing, do you handpick songs? I'm interested in finding out if anyone in the macrumors community has a better system than mine: I have a playlist that randomly selects songs that are rated above three stars upto 3.4gb, then have a playlist of any songs added in the last week. This usually leaves me enough room for podcasts, but not always. (iPod nano 4GB) So how do you do deal with it?