Before you buy an ipod listen to other players. Ipod is the most popular player because it is the most popular player. It's simple and it works. I'm not saying it sounds bad. It's fine. But there are other things that sound better. I tunes is probably the best proprietary software though. Gigabeat room, SS, and the mrobe thing are much worse. Why can't everything just be drap and drop and support playlists on the fly? Seems like that would keep development costs down.