I also have a wait until November.
If I pay the higher $399 price with 2 year contract, I'm going to want my upgrade eligibility to still be for November. That way if in 6-12 months when a new iPhone comes out, I could finally upgrade for the lowest price.
And that's the way it was before with the first iPhone. If you were eligible for an upgrade in one month, and you buy an iPhone, you'd still be eligible for an upgrade in one month.
Though, that was written before a subsidized iPhone was available. And now they are coining the term "Early Upgrade" for those that are not upgrade eligible. I fear they may still call it a subsidized phone at $399 and try and reset your eligibility for another 18-24 months.
Which would be BS, that $399-$499 is the same price everyone was paying before, which didn't effect your eligibility, and despite even that, they made all of them instantly eligible even if they bought a free phone before getting the iPhone. If as an existing loyal customer I have to pay $399 now, and in a year still have to pay $399 again for the new model if they reset my eligibility, that's like stabbing their own customers in the back twice.
Still, the ATT iPhone FAQ says there's no penalty upgrading to an iPhone, your eligibility continues from your last contract. But it oddly says for discounts on devices other than an iPhone. But that was written at the launch of the first iPhone, where there's was no discount allowed on the iPhone.
http://www.wireless.att.com/learn/iphone-faqs.jsp