Seems you made a few mistakes. I would never exchange rent for work etc.Freelancer, it sounds like you have had some rental properties. I will share a few of my experiences as a landlord. I would never be a landlord again.
The first go round was a building I bought in 1980 that was on the main street of our little town and had what I wanted to use for offices on the first floor and an apartment that I could rent out for enough to cover my costs on the second floor.
First tenant was a gal who was about 5 foot tall and 5 foot wide and was on section 8 which meant the government would be paying most of the rent which sounded like a good thing. Once she moved in I picked up all kinds of stories about her moving her sister into the last place and nearly burning it down. All the neighbors were upset with me because they felt like she was running a house since guys were running in and out all hours of the night. I got rid of her and got what seemed to be a nice young guy who was recently divorced. Well it turned out he was gay which doesn't bother me but the neighbors were again complaining about guys running in and out all hours of the night.
The same building had two garages behind it that I also sometimes rented out. I had a reasonably well dressed middle aged guy who stopped one day and wanted to rent it. He said he had been a pilot and was starting a business to sell some specialized airplane parts and needed a place to store them. He also said his money was tied up in inventory so he would give me a small amount of rent and would put new doors on the garage and do some repairs on the roof which were needed anyway. That sounded ok. Well I saw him back there all the time and he did do the work on the roof but never did the doors. About 6 weeks later I got a citation in the mail. He had moved into the garages and was using a bucket for a toilet and I was charged with renting a place that was unfit for habitation. Of course until they told me I had no idea he was living there but that cost me $ 400.00.
This isn't my rental property but involves the same guy who said he was going into the airplane parts business. About a year later I was driving home and saw a fire. I saw that guy standing there and stopped to see what happened. He had rented an apartment above an empty store (probably never paying) and his electric was turned off so he was using a coleman lantern for light. His apartment had wasps and he swatted a wasp, knocking over the coleman lantern and burned the place down.
A few years later I bought a house actually for taxes that had the potential to be a nice house. I mentioned that I bought it to a young couple that I bowled with in a mixed couples league and they said when I got it done they would like to rent it. Actually they offered to help with the remodeling if I would discount the rent a bit and despite the fact that he didn't know which end of a hammer to hold did that. At the time they had a small white cat. Once they moved in they got two big boxer dogs. One of the funny parts was one door had the upper part in glass and had a mail slot just below that. One day the mailman was putting mail in the slot and one of the boxer dogs came flying through the glass. They moved out after a couple of years. The new wall to wall carpet was ruined from the dogs and half of the remodeling needed to be redone.
About that time my mother turned over a small house to me that had been a rental property for her. My son was living with my ex and I really thought that had to be tough for a single guy so I asked him if he wanted to rent that place for enough to cover the taxes (60 bucks a month). Well he got a black Lab but being single he was never there. The lab destroyed his furniture, his army boots, his pool table and everything else he owned. It had no place to go to the bathroom so it went in the house. Even after ripping out the floor and part of the walls the place smelled so bad I would't go in it for 6 year and never did rent it out again.
The last place I lived in had a renter next door. They were really trashy people and were drug dealers as well. I heard them outside one night at 3 AM swearing at the landlord because their toilet was stuffed up and overflowing and he didn't want to come until morning to work in it. I sold that house last November and had a terrible time selling it because of the neighbors. I ended up getting 10 grand less because of them.