I'm experiencing this same situation right now with one of my (inherited) residents. I set the "late" date to be the 7th of each month because they told me they don't get paid until the 7th of each month. Well, after a few months of waiting around for payment past the 7th, I've (finally) gone ahead and started assessing late fees. This month they paid an extra $90 in late fees ($50 for past the due date and then $10 per day for each additional day). So, despite the small hassle, I got an extra $90 paid to me this month. They now are crystal clear that the late fees are going to be assessed each month going forward. If they want to pay me what amounts to at least an extra 7% in rent each month, then I will go ahead and take it. It's easy to bill them for this as I use Cozy.co also. I have not had to spend a dime to fix up their unit since I bought it, so I think I'm not going to rock this boat. Let them pay their late fees. Their inability to plan/budget is my extra 7+% revenue gain.