Problem tenant who pays their rent

[Nathan B.]

I currently have a 1rst floor tenant who has been a reliable payer of the rent for the last 2.5 years. They pay 1050 for a 3 bedroom apartment that currently would rent for around 1450-1500 in the present market.

The location is Connecticut and there is no rent control in the town. Currently they are month to month, and I’m working on another renovation above them and have a third apartment that is vacant at another property that is slow to fill this time of year.. so I need the cashflow currently until feb-march of 2023.

There are issues with this tenant. They are getting 100 a month off to do landscaping and snow removal that they do not do (they do the paths but not the driveway.. they fill the garden beds with knick knacks but don't remove the leaves... theres always an excuse, and they’ve claimed they can’t afford to pay the extra hundred). They are 60+ years old and waiting on a major leg surgery and have various health problems. They also smoke in the apartment, have trouble remembering to fill the oil for the furnace, and have friends drop by unexpectedly during the day who park in ways that block the driveway who they smoke with while I’m upstairs working on the renovation.  They're using storage on the property thats not theirs to use as well.

Until march 2022 the eviction moratorium in Connecticut made this person impossible to evict or end the lease.. and I had 3 apartments to renovate and re-rent this year that have basically stopped me from doing anything with them (still getting the rent every month and vacancy is more of a problem to me than a paying problem tenant).

My question is this: am I better off just doing an end of lease with this person with a 30-60 day move out time (I’m waiting until around march to do anything.. too many ways in the winter that this person could try to sue me for a convenient slip and fall or do massive damage to my property by “forgetting” to fill the furnace). Or am I better laying down the law sooner or later with a cure or quit with a rent increase to see if they shape up and fly right?  I am pessimistic about their ability to pay more rent or to adhere to the lease... I’m trying to get them out the easiest way. Is it easier // cleaner to remove a tenant with an end of lease than any other option? Do I need to give any explanation to them if this is the case or can I just say “I know its hard but this is a business and the investors want to end your lease” and leave it at that? I’m sure I am going to get peppered with ‘why!’s and ‘how dare you!’s and rationalizations if I try to explain why they aren’t the greatest tenant in the world and it seems like an end of lease with a timeframe they have to be out by is the easiest way to do it. Any advice would be appreciated. I already realize I’ve set a bad precedent with this tenant and am enabling their behavior.. again in some ways I had little choice during the eviction moratorium and managed to have tenants above them that didn’t mind their smoking… and I am currently dependent on the cashflow they are providing for the next couple of months.  I'm grateful to have survived the eviction moratorium without losing everything and they were a reliable tenant during that difficult time.