My old 60 gig iPod sync'd up fine with my iTunes: I had enough songs unchecked that there was enough space. But that one fried, and I got a replacement that I am having trouble with. I've unchecked a ton more songs, but it still says I don't have enough space, do I want iTunes to pick which songs go over. Well, last time I did that, it didn't take any of my playlists. So I want to control what goes over. But the problem with iTunes is you can't separate out the unchecked songs. I have no idea how many gigs are checked songs, how many are unchecked, and how much more I have to uncheck in order for all the songs to fit on my iPod. How do you experts handle such a dilemma? My iTunes folder has 58 gigs of songs, the iPod has room for 55 gigs.