I spent about two hours trying to order 3 phones on a new ATT family plan on the apple store to no avail.. finally gave up and went to AT&T and got everything ordered in minutes without any problem. Hope it ships as quickly! Glad I switched gears when I did, too, because now it's saying that you need to go into the store at Apple to start a new ATT family plan (for me, at least).
I also was wondering about the AppleCare+ situation--that was the main reason why I was so reluctant to order directly from AT&T, since I too couldn't find an option for it. I really hope we'll be able to buy it separately later..