iPhone?

I'm thinking of getting an iPhone. Not that I make many phonecalls (I'm more likely to text) but I think really I just want a cool gadgety thing like superheros had in the 1980s. I would also be very likely to use stuff like the camera and web browsing and Twitter apps.

I know one person in RL with an iPhone, he loves his iPhone but part of me thinks he'd be worried that if I got the latest version, he would then be less cool because his is an older model.

I know it's a big chunk of dosh but I reckon that's fair game for what you get, if you get the most out of it. My main concern is managing it through iTunes - I can quite happily manage a single iPod with iTunes, but I forsee things getting complicated, especially when the time comes to replace my laptop (which I'm hoping won't have to happen until Windows 7 appears).

Any thoughts, experiences anyone has to share? Will be most gratefully received. Thank you.