I walked over to the Western Union area (the same place you return items to) and asked for a Money Order for $999. I did not mention that I would be paying with two cards. I swiped the first card and was approved for $500 from the first card automatically. The POS machine asked for a new form of payment so I swiped the second card and was approved again. Success!
Next, the cashier asked for the card and my ID to check to make sure they are the same. Well, the card doesn't have a name on it. I showed her the card and said there is no name, but I pointed to the "Debit" sign on the card. She had already charged the card so she said, "ok, I guess."
Moral of the story: Don't mention anything unless they ask beforehand to see the card. Just start paying. Just like every other deal, every store manager can have their own rules. If they say ask for an ID, say "Ok, thank you," leave and come back when another manager is working. The same thing if they say Cash only (my brother reported this).
Technically, I could have bought a card for $999.01 since the fee is $0.99, but I thought that would sound awfully strange and my goal is always to stay under the radar.
Coming Soon
Hmm, working on that now. We'll see where that goes. Stay tuned over the next couple of weeks as I experiment.