>Back then, the trick was to get a generic Vanilla Visa or other prepaid credit card. A recent legal ruling meant they had to be run as a debit card for... reasons... I forget them.

Interchange fees, probably. Otherwise the credit card companies is taking a 2-3% cut.

>So you'd call up the issuer and have them issue it a PIN. Then you'd run it as a debit card and buy a 500 dollar money order.

I don't know how this ever could have worked considering that "cash-like transactions" are counted as cash advances, same as if you were to use your credit card at an ATM.