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 :)