For what it's worth, this is what I found out. I have 4 ipads I use for business. If you set up wi-fy accounts on each ipad using the same account number, it transfers the "usage" from one to the next. Naturally, I'm thinking that using my business ATT account is the way to go, but it's not if you are using the ipad to set up the account. MAKE SURE YOU CLICK THE BUTTON THAT SAYS YOU ARE NOT AN EXISTING CUSTOMER!!!! Otherwise, you will have this problem over and over.
It was set up this way because they originally thought it would benefit those who were updating from ipad 1 to ipad 2. Once it "transfers," and the 30 days expire on the first ipad (for me), the sim card on that ipad is invalidated. They will give you a new sim card, but there is the hassle. If you plan to use more than one, on the same account, before you set up service, go to ATT and consolidate the accounts from the beginning. The same terms apply - meaning no contract and month to month - but for business, if you run over, service won't stop. It will add overage, but you get the benefit of quitting when you want, so there is the plus.
Bottom line: it works like any phone with a sim card. Once you add a new one to an existing account without adding a new line - your old sim card is dead. I hope this helps. Pamela at ATT was very nice and helpful to me, and I have no complaints. This is not a perfect world, and we are spoiled when things don't perform perfectly. Treating people with respect will get you what you want. Good luck!