I have this problem. I have alot of music to manage (~130GB all full albums) and I would like to create a "smart" playlist that will pick a random album from all my music if the album has one or more songs with playcounts greater than or equal to 1. I have not yet listened to all the music and would like to discover it albums at a time. I asked a few people at the Apple store, I have seached Doug's apple scripts to no avail. Am I missing something or is itunes incapable of this kind of inteligence. I wish I could get itunes to put these albums on my ipod. I also have another issue, I have all my music on an external drive and I would like to reinstall OSX but I do not want to lose playcounts or ratings, is there a way of imbeding this information into the .mp3/.acc file. I know that I could just save the itunes library file but is there another way?