You could check if a cash advance would earn the miles, but be careful about the fees that might offset the value of the miles.

The fees for a cash advance would cancel out the value of the miles. We use that card for everything too, but never take a cash advance.

I cannot think there is any way to do this that wouldn't have your miles offset by the fees.

When we've made major purchases (cars, big landscape projects), we have always been limited in the amount we're allowed to put on the card (car dealer capped it at 5K, etc.) because the merchant has to pay a fee for the card use. Our last landscape project, I made a deal w/ them where I agree to pay the whole thing in cash and they discounted the project by 1.5 percent because their CC fees were higher than that.

There is no "way" to do it, it is simply a matter of whether a vendor takes cards, or not. We did once buy a Lexus SUV on a credit card, all of it, but that was a one time promotion with the dealer and Amex. The vendors pay a fee. The fee can vary greatly, usually the more business a vendor has the lower the fee. In day to day transactions with very large companies, the fee is invisible. (in fact generally most card agreements prohibit differentiated pricing, otherwise there would be no credit card business). With a proprietor, it is very much visible to them. He will probably do it if you paid the fee but, guess what ... the fee is going to be more than the value of the miles. I might only do this if I were very close on miles to a trip I wanted, and it was cheaper than buying them. Usually, the most economic thing to do with a sole proprietor is to pay cash ... no fees... and hey, I don't file the guys taxes.

Maybe you offer to pay the additional 3% (or however much) fee they are charged for you to use your credit card? (if they are even setup to take credit cards at all). I used a supplier who took credit cards but you paid 3% less if you paid by check or cash.

I am researching Plastiq now. My DH will need to do the math to see if the fee will be off-set by the miles earned. They are running a promotion that may off-set the fee even further.

Could you buy him gift cards for the amount owed? Amex often waives the purchase fees. I think you can get up to $3,000 per card.

This is not an individual person - it's a large design/build firm. That's why I find it so odd that they don't take CCs.

I'd guess that they wouldn't want the possibility of a charge back which generally favors the customer. I can certainly see that as a reason not to accept credit cards.

If only I could have used a cc to pay college tuition!

Apparently Plastiq was started by someone wanting to pay college tuition with a CC. They do have promotions that offset the fee so it's worth a look.

Plastiq looks interesting. Do your research carefully because it does appear that some payments can be treated by your card as a cash advance not a purchase, but Plastiq should always advise you. You do not want cash advance, typically no reward points, a one time fee, and no grace period on credit card interest. This seems to occur more with Visa than with MasterCard and is do to specific Visa reg.