There's a few services that will act as intermediaries for you like https://www.plastiq.com/ which charges 2.5%. I learned about these services on Slickdeals in a discussion on how to quickly rack up credit card reward points. A Google search turns up this list http://www.doctorofcredit.com/complete-list-of-options-for-p... (I'm not affiliated with the author).

Ya, I've seen these. It seems like the fee would likely be more than the value of the reward making it a losing proposition? Just wondering if the OP found a better way.

The land lord I use allows paying with plastic. There is a ~2% fee. It's better than a wash financially, but just barely. But it's net win for me even when it's a wash because I don't have to worry about mailing a check every month.

FWIW in months when I buy expensive plane tickets or make reimbursed purchases I skip paying rent with the CC.

If you just don't want to mail a check every month, you don't need to go as far as a credit card and paying a 2% fee. Your bank should have a bill-pay feature, and they will cut a check and mail it on your behalf. Usually this is a completely free service and can be done on an automatic schedule.

These services are routinely awful and incompetent, however. Also, you're relying on the postal service actually delivering the mail, which is often a dicey proposition.

Bank transfers really ought to be easier to do than they are.

I helped a landlord I was working with on other projects set up a basic Stripe form on the website for one of their properties. No subscriptions or automated payments, you can just go to their site and send them money via credit/debit card.

They eat the couple percent in transaction fees. In return, almost all of their tenants now pay online and instead of the property manager chasing people down for money, everyone generally pays on time (or, in a number of cases, early).

Depending on your priorities, "not having to chase people down for money every month" might be worth paying the $500/mo.

I haven't mailed a rent check in quite some time, my old property management company used paylease to accept online rent payments ($2 fee to pay with ACH, but at least I didn't have to mail a check). My current rental I just pay the property owner directly through Wells Fargo SurePay to her Chase account, works great and no fees for either of us (which makes for a happy me not having to mail a check, and a happy property owner who doesn't have to lose a cent of her rent just to accept payment).

I do not miss mailing checks in, and I do not wish to ever do it again.

It pretty much has to be, by definition, otherwise either the service or the card company would be losing money. It generally only works out if there's a loss leader that you're taking advantage of, e.g. many card companies offer occasional rewards at a loss to encourage people to use the card more in the long term.

How do you make this profitable with a 2.5% service charge?

You only use it to meet the spending requirements for the signup bonus. For example the Slickdeals home page has the Chase Sapphire right now: "50k Bonus Points ($625 towards travel) w/ $4000 Spent in First 3 Months of Account". Other cards have similar spending requirements.

My apartment accepts payments by card, but they pass the processing fees to the renter so it costs like 3% extra, which more than cancels out the CC rewards.

My last apartment had the same option, so I think it's pretty common.