well, if you dont have any mp3 player at the moment, i would say get the ipod, cuz its very nice to have while skiing. But if you already have a working mp3, i'd say skate 2
Get skate 2. Dont have your heart set on a shuffle. I got a Sansa Clip mp3 player for $10 on woot.com. It was only 1gb but they have had some other sweet deals. Just keep your eye out on woot.com sellout.woot.com and fatwallet.com and they have some cheap small size mp3 players.
i would go with Ipod, i didnt like skate 2 that much, gets boring playing bye yourself, if you have live and friends that have it then maybe, Career BLOWS hard.