I would have a talk with him & just say "hey I can save you a bunch of money by setting you up with automatic payments" & maybe show him how much he's paid in late fees.

You don't need to mail them, but you can or you can email them automatically.

Banks automatic no's.

This software is so affordable and has features like: automatic payments from your tenants bank account, tenant screening, publishing vacancies to sites such as realtor, zillow, Craigslist, etc., and keeps individual spreadsheets for each of your properties.

I have one tenant who has electronic transfer setup on automatic and two that send in checks. 

Setup your bank accounts so that the rent is automatically deposited to a bank account each month and the credit card is automatically paid from that bank account each month - whether the bank pays the card or the card pulls from the bank, whichever will allow you to pay more than the minimum.

If they have been through the housing court system, that's an automatic no.

@Ola Dantis Yes i have no issue with them asking first, that seems like an automatic courtesy.

There is an asset entry worksheet from where it will automatically flow to line 18.5.

There is, to that extent, automatic price support for such bonds.