most people cant/wont be able to afford a 30 gig music player with firewire, the parts are expensive and everything, so it would be at least 6-700 dollars for the new ipod, not a good idea in todays world. Also apple released airport for windows so i think itunes for windows isnt to far away, but really just pick ans choose your songs, i have an ipod and it only has around 200 songs on the 600 i have. This is because i choose what i like out of my cd and put that on my ipod, not the whole cd cause it would overfill the ipod. So the ipod is good only for the songs you will lisen to, not for the ones with dust on them. The best would be an ipod with 10 gigs in the end of '02 or the begining of '03, at best. So i would recomend that you get an ipod over auctions or one right from the store and buy the additional hard drive and put the new hard drive in the ipod and use the old hd (after you clear it) as an additional hd, 5 gigs extra cant hurt, but go to ipodhacks.com or ipodlounge.com or ipoding.com, and see what they have done before anything so you dont buy an extra hard drive for no reason. an alternative is get a cheapo 200 dollar mp3 player with lots of space but with a cheap hard drive, bigger, usb, and more difficult controls. I say the ipod is better for looks and works. Also not many mp3 players are that big, only about 4-7 are as big as the ipod hd is so dont go around complaining. Get the pod now and update it till it cant be updated anymore, thats what im doing. Also, asurace what you speak of should be a really good pda so get that when a great one comes out cause thats really not an mp3 player after all those changes. but for the me, 5 gigs is more than enough to keep me happy, also just think how much easier it is to use the ipod then all those cds.