Just crossed a year with an iPhone, and a couple of weeks ago, got a second thanks to being part of a work pilot program. So I carry two around...
I also hate the otterbox cover, as just mentioned, not only is it bulky, it also gets a TON of lint. One of these days, I'll replace it. One other thing that I don't like about the otter case, the ear feel- that edge really pushes on your ear oddly when you are on the phone.
As a phone, they sure have a lot to be desired for. Especially the battery life. As a tool, the more I use them, I'm finding a slot for one. I got my personal one just before going to Europe, and having it over there really was nice. I managed to get it unlocked, which meant that I just went to a store, got a new SIM card, and done. And as a traveller, a mini computer with GPS is really, really handy. Especially if it also takes really good pictures. And plays music. And gives me distractions (games, books, web surfing, etc).
I have learned to deal with the battery- between chaning the power requirements to being used to charging it. Tolerable.
My new work one is interesting. Being a work phone, the apps you can get are very restricted. So basically it's a phone I can read my e-mail and have as a planner. That IS useful, but it should be better, I think. Needs some document stuff (again, apps are through work only, so I can't just get them from iTunes).
I think I can go back to not having a smart phone. But having a device that does as much as it does is pretty nice. The work one- we'll see. But I hear that everyone will get them. Why? Dunno.