Despite the grumbles about iTunes, this is the program that most of us must use with the iPods that most of us have (if we have a digital music player). So I thought it would be useful to have a thread to share useful tips & tricks for iTunes, our iPods, and maybe helping each other work through some of the frustrations with their quirks. My biggest revelation was that Playlists are central to managing content on my iPod, having more music than space. That then resolved my frustration with the iPod lacking a means to randomize a playlist. I found it was done by randomizing the playlist within iTunes; the random order is preserved on synch in the iPod. If I get tired of that order, hit the random button again in iTunes on it's updated on the next synch.