Training Tenant/Constant Late Rent Payments

[Dominic Scatto]

Hello Fellow BP'ers!

So, I've been renting to the same tenants going on 3 years! Exciting, yes. Everything has been fairly uneventful with them - except for having to replace the whole HVAC system the first summer they were in it because it failed (not their fault) - and they do take really good care of the property, they get along with the neighbors, and have even fixed a couple things themselves - like a leaking toilet. Great, right?! Well, about 3 months in, they were late with the rent. No big deal, they gave a reasonable excuse, but then it became a habit. Now, I have noticed that they are on the same pay schedule as I am with my work and have always made the rent payment no later than that following paycheck. So, it seems more of a lack of budgeting. However, that's not an excuse and I know I should've nipped it in the bud. 

Any who, I'm getting ready to move and rent out the SFH we're currently in and I want to do everything right from the start on this one and fix the issue on the current one.

So, my question for the problem child is, would it be fair to offer them two options: 1) Keep things as is - not enforcing the late payment, but raise the rent $50/month or 2) Keep rent the same, but enforce the late payment policy?

Things to note: I have not raised the rent at all in the 3 years nor have I charged them a late payment. Reason for the lack of rent increase is I'm charging a fair amount,  if not just slightly under market value, based on my area and the size/square footage of the home. I technically could raise it a bit, if I wanted.

Thoughts/Opinions/Suggestions?

Thank you all, in advance!