Citi AA Exec MC MS: Paying contractors?
 

I am planning to apply for the Citi AA Exec MC, primarily for Admiral's Club membership, use as a business card. Based on the continued devaluation of AA benefits, lack of bonus spend categories for the card, I focus business spending on Chase Ink, AMEX Hilton, Citi Prestige, reluctant to go through the hassle of modifying auto-payments to meet min spend. From this perspective, I will not be able to meet the enrollment bonus minimum spend, standard manufactured spend strategies aren't of interest.

My company has 2 independent contractors, who are paid on a monthly basis - more than enough to easily meet the minimum spend in 1 - 2 months. They are typically paid from the company's checking account (Bill Pay), I am wondering if there is a no/low risk, minimum hassle, no/low fee option to do so by using the card, where the spend will count toward the enrollment bonus minimum spend.

Best option is to ask the contractors to take a credit card payment.

You can pay them through Plastiq for 2.5% but you will need 10-14 day lead time.

Neither is risky.

Alternatively, you can go the MS route of purchasing GCs, converting them into MOs, depositing the MOs into a checking account and paying them with a check (assuming they refuse a CC payment).
I am in your boat in that many of my creditors do not take plastic. I have a special checking account just for them where the above is done.
I have calculated the cost of paying them in this manner is (without special sales or going through multiple payment portals, etc) to be 0.8%, which is a whole heck of lot less than the Plastic 2.5% or other "convenience fee offers" ranging from 2%-5%.extra over the base payment.

Can you ask them to get a Square reader (for ~ $10), and pay them 2.75% more than the invoice to cover the fees?