First, I apologize for the length of this post, but I feel some background is needed.

Early this year I purchased a Triplex with 3 occupied units.  None were on leases so I got 2 of them signed into a year lease pretty quick.   The 3rd had a history of violence towards the other tenants and had anywhere from 8-12 people living in a 2/1, so obviously had to go.

1 of the remaining tenants in a 1/1 first floor Apartment is a single male

He has lived in that Apartment for 15+ years, and the previous owner did not pay a whole lot of attention.  This Tenant, in years prior to my purchasing the property, without permission from the previous owner has done at least the following:

• Added a Swingset for his daughter who used to live there
• Built a extremely not up to code shed attached to the back of the building which looks terrible.
• Completely took over all of the interior common space and back porch with his stuff
• Brought a Cat into the property
• Parked an extremely dilapidated boat which has been used as a garbage container in the past, on a trailer with flat tires in the yard
• Wired a power line into his fuse box to run a line to the enclosed back porch
• And the last I know of, but by far the most entertaining, wired a power line from his fuse box into the common space, and back into his bathroom to power his...  Shower head.    Yes, he had LIVE exposed wires twisted together with no plastic cap hanging in his shower for years.   Why?
• He has never paid his gas bill, so the heating system in that apartment has not been used in 15 years.  Instead, the previous landlord installed an electric hot water heater so the sale could go through.
• Has caused the pipes to freeze in the walls by not keeping the door between the common area and the enclosed back porch closed.
• He heated his apartment using 5-7 electric space heaters.  (This building has old wiring.  The wiring would not support the amount of power the breakers were set for, so the wires would catch fire and burn before the breakers would ever trip.   This has been fixed now as I saw that as an emergency issue)

The Furnace for that apartment is located in the Common area, so using the furnace, and keeping the door closed between that common space and the Porch will prevent the pipes from freezing.

When I got him on the lease, I gave him a pass on the boat... for now, and the Cat, and informed him that a lot of things were going to be changing, and that he needed to clear the common areas of his stuff.   The Lease also states that Gas Service is a mandatory utility to be setup in his name, or I will pay the bill and charge the amount back to him, along with an additional fee.

I told him that because the Gas lines and furnace have not been used in so long, that I would cover the initial setup cost and the first months gas, but he had to move it to his name.   So, I got recently got the gas service all setup and working, and covered that first month.   This allowed me to verify that the door being closed in the common area, with the furnace running, would be enough to prevent the pipes from freezing.

However, the Tenant has turned the thermostat all the way down, but still on, and I believe is still using the space heaters to supplement.  In addition, he keeps leaving that door between the common area and the enclosed porch open, causing temperatures to further drop in that room.

Now, he is complaining now that because I had the electrician disconnect his shower-head water heater  he can not take showers and has to go to his mothers house as the water will not stay warm long enough.   That apartment has a brand new electric water heater.   I am sending the maintenance company over to check on that and will fix it if that is actually an issue, however I have a hard time believing anything he says.  

He claims to be a contractor, and that he is currently building a house, but since pulling the power from his shower-head and getting the fuse boxes properly wired, he has called me for multiple issues such as the lights in his kitchen flickering... which turned out to be bad bulbs. But, he did not contact me about the fact that his toilet is running constantly which I found when I was there last (I pay the water bill). 

The upstairs apartment had a cockroach problem, which I took care of, and asked the tenants in both lower apartments if they had seen any sign of bugs.    Both said they have not.  1 of them keeps his place spotless, and this tenant does not.  However, he said that he had not seen any sign of anything.  However, when in there recently I moved 1 piece of furniture and they were everywhere.

In addition, his rent is routinely a few days past the 5-day grace period, with a complaint that the mail must be running slow (Even though his envelope is post-marked AFTER the grace period is over) He is trying to pay 1 month in advance, but every check he sends each month is anywhere from $10-60 short of covering the next month + the late fees.    For example, for him to be paid through December, he still owes $40, or $465 (low rent because he gets a credit for handling lawn/snow for the Triplex) if he wants to be paid up through January.   I could for example on the 8th of December receive a check for 450, meaning $40 in late fees will have accumulated on that $40 he owed to be paid up for Dec.... and poof, he has late fees due Jan 1...  even though he will only owe 15 to be paid in full for Jan...   and on and on it goes)

For Nov rent, I made an appointment with him on Thursday to pick up the rent check on Tuesday after work, which was technically 1 day after the grace period, but was going to forgive the late fees that time because arrangements had been made to pick it up... When I got there Tuesday he was not home.  I waited approximately 15 minutes for him to get home from work and sent a text.  He did not respond for another half hour.  I assumed maybe he was driving home.  When he did, he told me, 'I am at the movies.  I mailed the check on Saturday'.   That disrespect of my time was the end of my patience with him. He could have told me at any point he mailed it as he knew we had a set meeting time.

I know there is a learning curve in going from being the person who ran over the previous landlord constantly to me who does actually pay attention, and he actually has improved over the time I have had the property in many aspects, until I had his shower head disconnected.  His 1 year lease has another 8 months approximately left.   

I could Maybe file for eviction based on a couple minor breaches in the lease, such as being a few days late on rent, not having renters insurance, his likely not putting the gas in his name soon, leaving the door in the common space open, not notifying me of the bugs, and leaving all his stuff in the common area...    But, these all seem like minor issues and I am not certain if an eviction would even be able to go through based on this stuff.  And if it does, his apartment is going to need some reno work before its re-rented as its a bit of a mess too.

Anybody have any thoughts\suggestions?   I am worried about more vacancies, but at the same time, worried about frozen pipes damage...

I know that this is what property management companies are for, but as this is my first investment property in which the most expensive apartment was vacated shortly after purchase and has not been ready to re-rent until this coming weekend due to a ton of renovation needs, the property is most definitely in the red and with the credit cards hit from the renovation, its going to take a while to get this property to a point where its making a profit.    It WILL make a good profit, it just took far more up-front capital then expected with the reno and the long vacancy in the most expensive apartment.