It took a while, but I hope I finally got the attention of my always last to pay tenants. They are 3 year tenants and did ok first year and a half, but started slipping in 2020. Then came moratorium.

I always send a text on 2nd reminding any late payers. "Rents are due on or by the first, late fees begin tomorrow at $5 per day you are late." They stopped letting me know before 1st if they would be late and with my warning would text back the date they would pay. I have been charging full late fees and for past 4 months, they have not paid until the 15th to 19th with late fees capped at $75, so I am getting more money from them. I have been having them sign in person a 10 day pay or quit that expires a day or so after promised date, but it just does not register with them. This month as usual every tenant but them paid by 2nd, but I sent no reminder and they sent no text telling when they would pay.

I had the Sheriff serve a 10 day pay or quit today(Will be able to file Monday the 17th) and at same time notified the tenants by text they were receiving a 10 day notice and I was putting a hold on my bank rental deposit account and would only accept full payment in person during the next 10 days to avoid eviction. They did not pay full late fees last month so it became rents this month.

They replied in shock, we are going to pay on the 15th with full late fees, we have children ,you can't evict us. Guess they think they moved rent day to 15th. I replied you are slipping behind further all the time and it will catch up with you because rents are due on/by 1st always, and if you continue to slip you will get evicted. They sent back they would pay full amount with late fees and start paying on first from now on.

I am not going to bet any money on their keeping the promise, Hope I can keep them paying rent and heat until nearly spring, then end their lease.

Good job! Being firm is the only way to be to get the result you desire.

I became complacent with some tenants I once had many years ago whose rent slowly started appearing later and later. It finally dawned on me they had trained me to accept rent late instead of me training them to pay it on time.

I learned from that mistake. Even though I seldom get requests to pay late now when I do, I still post a three day pay or quit notice which I tell them is required by law. This way I’d they don’t follow through and pay as agreed I don’t have to delay their eviction because they’ve already been given formal notice by law. So I tell them although it gives them three days I will hold off on filing it with the court until the day we agreed on for rent to be paid.

A few things I have found to work - sometimes - is if someone continuously pays a bit late, ask them if they want to change the day rent is due. If so, pay the pro-rated amount necessary to take them to that date once, and pay on that date from then on. No biggy, no magic about the first. When CAN you pay? Pick a date - and then STICK to it. No more late fees.