@Dennis M. The guy has definitely had a ton of bad training. Oh I have no doubts this property will turn around. Just need to get past the current issues.
@Nathan Gesner The property was in need of some serious maintenance and cleanup when I got it, which is part of why the upstairs unit has been empty so long. Its been a bit of a base location for stuff while getting the property cleaned up, as well as renovating that apartment itself. There currently is only the 1 low quality tenant. The other guy is all good. Struggles a bit financially and rent increases may be a problem for him in the future, but he has never been late that I have seen. The rates on this place are not bad at all for the area. The bad tenant has a discount monthly for handling.
@JD Martin To your first and second points, I didn't realize all of this when he got that lease. Admittedly my mistake, I did not properly screen the existing tenants like I would new ones before I signed them to a new lease.
I was distracted in dealing with the 8-15 violent people in the large apt who were destroying the property and causing neighbors to reconsider living there. Every wall and door had holes. So at the time this problem tenant was a minor issue in the grand scheme, and I knew dealing with upstairs was going to take awhile and I needed a bit of income so the property could at least pay for itself.
In hindsight, I should have re-signed him to my version of the month-to-month lease.
To your third point, I don't go pick up the checks. This was a one-off situation. He was going to pay to overnight it on Saturday morning. I told him that I would be there Tuesday and he could just give it to me instead and that I would forgive the late fee as if overnighted I would have had it on-time. Cozy is the preferred method of rent collection, but this tenant refuses to set it up due to a fear of a past identity theft issue. I have the option of mailing a personal check in the lease provided its received by the end of the grace period. One bad personal check and they have to mail cashiers checks if they still can not use Cozy.
To your Fourth point, he had been handling building maintenance for years anyway with the previous guy. I told him that I would no longer allow that, but he could handle lawn and snow. The reason being, until I got these initial issues resolved and someone in the upstairs apt, the building is actually costing me every month. I gave him a $50 credit per month to handle the lawn and snow provided it was done well and I never need to give him a reminder. Its in the lease that addendum is cancelled in the event a reminder is needed. It was going to cost me a good deal more to have a company do it... But, I probably should have went that way anyway.
I had his deposit transferred over from the previous landlord, but there was no move-in inspection or any documentation except the prior 1 page 'lease'. So, with the new lease we got the move-in inspection done and had him sign a document regarding how the security deposit would be handled, so we are all good there.
I fully acknowledge that I am making some mistakes, but I am learning as I go on this.
I will likely try and ride it out a little while unless there is some new large issue or he keeps leaving that door open. At least until the large apt. is rented as I really can't have 2 of the apartments empty at this point.
@Andrew B. In the future I will likely have inherited tenants sign a new month-to-month lease, and transition it to a term lease later. I prefer to keep tenants on a term lease when possible with the stipulation that it will renew as month-to-month with a higher rent at the end.
I already have an attorney I am working with for any eviction proceedings that need to go through. Once I decide that it is the time to do it, I am going to give her a call and let her take it from there. MO is very landlord friendly, and a notice to quit is actually not required, however for me at least having an Atty handle that deal is.