Background: This was one of the first rental properties I purchased, so I made every mistake underneath the sun and I am still dealing with the consequences. I purchased this quad for $247,000. It is in Columbus, Ohio just north of The Ohio State University in a B location. I put about $30,000 into it and now I have it rented or about $3,700 but now it is all falling apart. 

Unit 1: 1bed 1bath - Tried to raise the rents from $350 but he could not afford it. I vacated it and paid a contractor way too much to remodel it. I have it rented out for $920 now.

Unit 2: Vacant. Got someone in there within 6 days for $800. We were not running background or credit checks and we had to find a new tenant after a few months. We should have stopped when she said she needed time to get the full deposit. We collected all of our rent, but she left some human feces behind that our cleaner had to deal with. We took it from her security deposit.

Unit 3: Raised rents from $350 to $750. I need to raise it to market rent which I think is $920 but I may just leave him for another year. I have too much stuff going on. 

Unit 4: The unit you have all been waiting for!

The Story: My college roommate and I were just getting into the real estate investing game 1 year after graduating college. We had house hacked a duplex and a quad in less than 4 months (we took turns getting the loans). We then took the rest of our money and got an investment loan on this 4 unit.

The 4th unit needed substantial work to get rented to the market value of $1,200. We figured we would offer the current tenant a chance to pay $1,100 as-is. He agreed and paid us rent on time for the next 8 months. When it came time to release, he did for another year. Shortly after releasing, he starts drunkenly calling me about petty things like the tenants putting trash in his trash can. He caused the bottom unit to flood by unscrewing his toilet water valve. Luckily, I fixed it in time to prevent a lot of damage. And now I get the below messages. What would you do? I do not plan to release him when his lease ends in July. How should I break the news to him?