Yes, you should. The iPod is acoustical evil in a white package. Personally, I'd recommend a pocket PC of some sort if you want to spend that kind of money. You get a device that can play real movies, do email, messenger, web browsing, finances, text editing, real games (eg Quake 2, etc), and with a four inch full-color screen for the same price. Just make sure to buy a large expansion card and you can fit tons of music on it. I've got five gigs in my HP HX4700. You can buy an 8GB microdrive for about $110...and that's a lot of music and movies.