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.