Tenant keeps paying rent late

[Alexander Rodriguez]

This is my first property, it’s a triplex that I purchased a bit over a year ago. One of the tenants, which was inherited by the previous owner, has been paying rent late consistently (for the past 4 months) and by late I mean at the end of the month (rent is due on the 1st). The people living here are a nice family, with a large dog, that I allowed them to keep with certain rules. For example, paying $25 every time they don’t clean after their dog’s poop. Which they don’t clean so it’s additional income haha. However, I noticed after an inspection that the dog has been peeing inside in a room, and there is severe damage in the floor. I never checked that room, so the damage was there probably before their lease started. Honestly, I am getting tired of sending notices every month and the $50 late fee (capped in CT) is not worth it. The only benefit I would say is what they end up paying for not cleaning the poop in the common areas/yards, which is an extra $200 to $300. I was going to also increase their late fee significantly or to accrue daily, but a new law in CT just set the limit to $50. (Apparently a new law to protect tenants, but this time is a disservice because it takes off the table what could have been a resolution to the issue, and might leave eviction as the only choice). Should I evict these tenants or is there a more peaceful resolution? Should I ask them to repair the floor first or increase their security deposit before evicting? Their security deposit is $750, and their rent is $1450. Their security deposit will not cover for the damage to the floor. I feel bad because I know they won’t be able to find a place to move with such a large dog. And they just had a newborn. They are renting month to month, and I talk about eviction because I know they will not move out peacefully, since they simply won’t be able to find a place that will accept a giant dog/aggressive breed.

[Nathan Gesner]

Quote from @Alexander Rodriguez:

For example, paying $25 every time they don’t clean after their dog’s poop. Which they don’t clean so it’s additional income haha. 

You are cleaning up after their dog and considering the $25 as extra income?

There are so many problems in your question. Urine in a room, but you don't know if it was there before they moved in? Do you inspect between renters? Do you inspect during renters? You told them they could have the dog if they "keep with certain rules" but then you don't do anything when they fail. Why do you keep a renter that pays so late every month? Why are you worried about their ability to find a new rental with a "giant dog/aggressive breed" but you are willing to accept that kind of animal in your rental?

One of these days your rent money won't show up at all. They will leave the place with thousands worth of damages, and you'll be cursing yourself as you pick up after their dog.

So many investors lose money through improper management. I highly recommend you give these tenants notice immediately. Start saving your pennies, because they probably won't pay everything they owe on the way out and they'll stick you with cleaning and repair costs. 

While you are waiting for them to leave, start looking for a property manager who can stop the bleeding.