Also, keep in mind a couple things: If charging to an SPG card, you can convert at 1.25 miles/point. Also, my understanding of the tax rules is that if a self-employed taxpayer, the 2.5% convenience fee is deductible, effectively reducing the aftertax cost of the fee.
Whether a substantial overpayment triggers a red flag I don't know. I was just throwing out a number...hardly in a position to make a $80K overpayment

... would like to overpay for the miles, but a realistic amount.
Goph