A few things I found irritating... first was Apple promoting the phone at $199 & $299. If they had simply said "new subscribers" it would have been understandable. It's very misleading, and I'm sure there will be lawsuits over it once the iPhone 3G S actually goes on sale. Of course, I understand the whole subsidizing of the cost. I didn't expect to be able to upgrade the wife's iPhone 3G to a 3G S less than a year after getting it. That's just common since... however, if AT&T were smart about the process, they would have offered the phone at a slightly discounted "full" price and then extended the original contract for another two years.
With a first generation iPhone, I am eligible to upgrade to the 3G S at the discounted price w/ contract. As much as I use the phone, the faster speed would be really nice to have. I've been sitting in places where I get no service, and the wife's iPhone 3G is at full strength. There is simply no comparison to loading sites in Safari, even sites that are not iPhone friendly (like OCC). Will I get the iPhone 3G S? Lord knows I want to... I really want to. Right now, I'm being held back by AT&T. I joined under Cingular, and have a very nice family place + rollover.... however, I'm not happy with AT&T's actions and network.
AT&T's exclusive with Apple expires at the end of the year. Word is that Verizon may be getting iPhone love starting in 2010. Would I switch my iPhone's to Verizon? Absolutely.
Though I have to say, I'm still pissed off at Apple with the iPhone 3.0 OS. MMS and video recording are not available on the iPhone EDGE due to "hardware limitations"? BS. Jailbreak your iPhone and you have those abilities. Other EDGE phones have those abilities. And it doesn't change the fact that Apple (and AT&T) should have included those features in the iPhone on Day 1. AT&T not supporting MMS until "later this summer" is stupid as well. They've known this was coming for a while now and they have had more than enough time to prepare for this roll out.
Tethering isn't that big of a deal to me. I've never had a need for it. WiFi is easily available these days (Starbucks, MacDonald's, Krystals, Panera, air ports, malls, etc.) if I need internet on a notebook, I'll find it... and cheaper than what AT&T will charge for it. - Ironically enough, WiFi at Mac D's and Starbucks is via AT&T.
I think the Apple keynote at WWDC gave clear message that Apple was not at all happy with AT&T. Those slides of iPhone providers that are "ready to go" had to be a slap across the face of AT&T management.
I love my iPhone, I use it more than my PC, Mac, TiVo, 360, PS3, and every other piece of technology I own. I'll be upgrading to a new iPhone at some point in time, just not sure if it will be with AT&T or some other provider in the coming year. Though my lack of self control will probably see me locked into a new AT&T contract for 2 years... which may not be bad, because by then 4G networks should start being rolled out.