This again?
I registered specifically to address this line of thinking--as AT&T is 100% wrong.
AT&T should cater to its enthusiast base, and figure out how to adapt to that which is a unique opportunity: being the exclusive US carrier of the iPhone.
Apple is on record as saying the iPhone will be a "summer event". There is clearly room for interpretation as to exactly what this means, but I, and others, expect an annual hardware revision.
Show me another device with an expected annual refresh of its hardware.
I was in line the day the iPhone 3G was released and I discussed the upgrade issue at that time with others in line. I hoped that AT&T would figure it out in the coming months. AT&T did not.
Part of the problem is "upgrade eligibility". It is not defined. You may be eligible for an upgrade 12-24 months into your contract. There is ample speculation on the contributing factors: length of service with AT&T (and its previous incarnations); monthly service bill; family vs. individual plan; number of iPhones on a family plan; credit and/or bill pay history.
One factor OUGHT to be considered: early adopter.
I recognize that the contract I sign with AT&T is for the service it renders, and I am beholden to its service for the duration of the contract, else I face an early termination fee. As such, AT&T knows my monthly bill minimum, and has reason to believe that I will continue to pay per my current level of service. That subscription fee ($240/mo), and the fact that I am a current subscriber, is what is of value to AT&T.
If the subsidy needs to be reworked, then do it. If the price paid to Apple needs to be modified, then do it. But, as some first-day subscribers are eligible for an upgrade on July 12, 2009, it is ludicrous to deny a service resubscription to the most adamant followers of a device. "Upgrade eligibility" is already a loose term; flex it to allow upgrade pricing for early adopters.
Doing so would demonstrate AT&T's commitment to the Apple/AT&T relationship, and people would be happy. Happy subscribers, and subscriber retention, is far more important than a slight hardware subsidy.
AT&T looked poor after a fine WWDC. The opportunity was there, and AT&T did not deliver with MMS or tethering. Granted, the partnership is on rocky terms, and each side is attempting to wield whatever power it may have, but the result of the tension alienates the enthusiast. And that's bad business.