I presume with Stripe you can only send from your Stripe balance, which certainly can be funded with credit cards (yours or others), but you'll pay the 2.9% + transaction fee on the "inbound" (CC) side, which (I think?) would cost more than the miles. In that scenario you could skip the debit card part entirely and just charge your own credit card and have the money go to your bank account.
The miles hounds have throught through these scenarios pretty thoroughly :)
One major bank set up an online payment service in the UK about ten years ago which allowed you to load money, fee-free, from a credit card, and then pay other people. Of course, said money, once loaded, could also be withdrawn back to your bank account, but why would anyone do that?
WHILE airmiles < MAXINT do { load, withdraw, pay card bill }
Round and round the money goes. :)
Obviously the fee-free aspect was unusual, perhaps an oversight but more likely an attempt to get some critical mass in the online payments market which, at the time, was primarily only PayPal and a UK outfit called "NoChex" (which of course DID charge a fee.)
Eventually a loading fee did arrive, and a little later on, the service closed up shop entirely.
When the dollar coin was first introduced in the US, you could order them online for no extra cost, as a way of increasing adoption. There would be a $1000 charge on your credit card, and 1000 coins would show up at your door (shipping was free too).
A lot of airline miles were earned at the expense of the US government.
More accurately, at the expense of us currency holders. The mint is self-finaning.
The cost to the mint to produce a coin is far less than the face value.
Whether anyone was actually hurt depends on how the cost to distribute this way compares to the normal cost to distribute new currency.
And, assuming this method was more expensive, calculating who was hurt and by how much would take me a few hours. Maybe someone else has that more on the top of their head.