My AT&T page says this:
You are not eligible to upgrade at a discounted price due to your length of service. However, you may still purchase a phone/device at the full price. Our records indicate that you will be eligible for an upgrade at a discounted price on 12/11/2009
You are eligible for an early upgrade to an iPhone at a reduced discount. Our records indicate that you will be eligible for an upgrade to an iPhone at a discounted price on 12/11/2009
It says that all on one page with two floating boxes. That would put the upgrade 1 year and 5 months after I upgraded to the 3g on iDay '08. I also bought the 1st gen on iDay '07. So apparently everyone has random upgrade times, which means AT&T is trying to confuse us or doesn't know what's going to happen yet. I think I remember something similar happening last year with the varying upgrade dates. This is what I expect to happen:
Not upgrade eligible: 16gb - $299, 32gb - $399
Upgrade eligible (6 months or so before contract is up): 16gb - $199, 32gb - $299
There are also rumors that the price might go down, especially with competition from Palm and Sprint, so maybe those who aren't upgrade eligible will pay more, but the same amount from last year. Those who are eligible will pay $99-199?
Also, if AT&T follows their normal routine of allowing upgrades after 18 months, and if the rumored AT&T exclusivity agreement expires in 2010, then all iPhone 3g owners will be upgrade eligible from January 2010 or later and if it's announced at MacWorld that Verizon is getting the iPhone, people may just decide to wait out the remaining 6 months of their contract and jump ship. I know I would seriously consider it, and I've been with AT&T for 5 years.
I know those are a lot of ifs, but with the Pre coming out, AT&T and Apple have to work together to make sure their customers "stick", even if they make slightly less money on them going forward, its better than making no money at all. It's better to take a loss than to lose it all. Now Apple will never lose it all, but AT&T could with its exclusivity expiring. Stranger things have happened.
I also think this new version is worth it. I've said all along that I would upgrade if only the battery lasted longer. From everything I've read, it most likely will. Battery tech is slightly better, the Arm Cortex A8 processor is supposed to have better energy savings, the 802.11 N wifi chip is supposed to be lower powered (something to do with send / receive at once instead of seperately?) Also the (low) chance of OLED display would improve batter life with no backlight. Not sure about the 7.2mbps new 3g chip, but maybe it uses less power too. Autofocus camera makes the images much more usable, especially in apps that scan barcodes, etc. Compass will be great in Google Maps when driving because it will reorient the maps based on heading. Double the RAM to 256mb will cause most all app crashes to go away, especially Safari. Matte enclosure also means I won't buy a case. Then don't even get me started on video...most likely 720p, since the Arm Cortex A8 supports that. That chip is also lots faster than the current one, even though its only 200mhz faster, the architecture is much better. The iPhone only needs a little bit of a push to make it blazing and keep down the small amount of lag. I'm also sticking to my statements from months ago that it will be called the iPhone Video (funny now that there is a rumor that is what it will be called).
Ok sorry I'm done with this novel. I'm bored at work today, finished all my projects a day early...