My struggle as a for-profit real estate investor/landlord vs. for-charity believer continues.. Here is one of my stories,

About 10 years ago, this fellow LH moved in with my section 8 tenant CL. He was looking for handyman jobs and I happened to have a unit in the same place that needed to be painted and cleaned. He proposed a price, I accepted and it worked out for everyone. That started our relationship.

Throughout the first couple years, he did many turnover jobs for me and it worked well for everyone. CL's adult son didn't report income and she couldn't pay back to PHA whatever she owed, her voucher was terminated and I had to evict her. That eventually led to this struggle of mine.

I was greedy and couldn't let go off his service. (cheap/fast/good) I put him in a finished basement I had and he moved her in. I turned a blind eye, everything worked fine.

At the same time, my marriage suffered and I temporarily moved into one of my apartments. One self claimed believer smelled blood and found her new target. I was gullible and ignorant, managed to let her into my life. Nothing sexual, but grossly inappropriate, I will shake my head the rest of my life for what I did wrongly. I introduced her to LH since they were from the same region. LH suffered a stroke and was hospitalized. She arranged the hospital visits and convinced me that it is a noble thing to do to let LH move into one of my units after he was discharged from the hospital. (Hospital won't let him back into that illegal basement apartment)

He largely recovered and was able to continue to do some work for me in exchange for his staying. His companion CL moved in with him. That was around 2019-2020 period. Before, during and after COVID, I sold half of my portfolio, paid off all debts and achieved true financial freedom. Maybe due to aging, his qualify of service deteriorated and I decided to ease out relying on him to do turnovers.

All the years he lived rent/utility/cell phone bill free till I was contemplating to sell this place. It's a small commercial building, valuation is hinged on the rents. Plus I am rebuilding my relationship with wife and family, wife reminded me that this has to end. I was also concerned about his cancer-survival-flailed-aging companion. I have no means of dealing with this situation.

After a mortgage broker did initial valuation, I decided to set a rent and start to charge him. The rent was below the market level, on paper, he pays utilities, in reality, I still carried. Between the 2 SSI incomes they should be able to afford it, however he has been behind ever since I started the lease 6 months ago. I helped him applying for senior housing a couple of years ago but the wait is long. We went through eviction court, in hope that this help him, but it didn't.

At this point, I was actively pushing him to find other affordable basement apartments in the area. All excuses aside, he claimed that he lost 2 leads and agreed to be out even with no prospect of a living arrangement. It bothers me because I am pushing him to be homeless, at the same time, there are so many homeless people out there whom I have no business in helping them (to justify my guilty conscious).

I realized that I am struggling with LH's situation because I know him. He grew up in a Christian family, his father was a womanizer pastor, no judgement here, but he was not interested in going back to his faith. I even thought about willingly funding his life if he is serious about his faith. What was I thinking? I don't know.

I want to conclude by thanking you for reading this messy personal journey/struggle. My wife is 100 times smarter than me and always remind me not to mix business with charity. We donate to charities, but I am messing up business with charity here.

PS. LH called me that he was ready to pack up his backpack and leave. CL refused to leave, too fraile to leave. I advised him to call ambulance and let the state deal with her. I feel that I weaseled out.

PPS. If I didn't believe in anything other than this life, I wouldn't have any hesitation or struggle, but I do.

I've struggled with these type situations as well.Only the details are a little different.

What I've decided is that if I am going to give someone a free ride, it's better to rent to someone else at full price and then donate the net proceeds to a charity that handles these type situations. The charity deals with this all the time and have much more experience, contacts, etc.

" Between the 2 SSI incomes they should be able to afford it"

I don't have any useful advise. I think everyone has done things that they latter regretted for various reasons. "It seemed a good idea at the time"

You are grappling with being fair and the fact that life is not fair.

there are things in life that are hard with no easy solution. I think at the end of the day you have to do what is right for you and let the chips fall where they may.

it seems that you are making progress doing that and just struggling with the falling chips.

You are not their daddy. You don't have to keep them up.

I too believe in a life after this one. I believe we are accountable for the choices we make. That is true for this couple as well.

Thanks for all the encouraging words.

After two years counseling , I learned a great deal about human behaviors and trauma theory as well as attachment theory.

As landlords we are leaders. We have core values and do what we do with a desired outcome in mind. In a perfect world, that path is ever so clear. The realty, this path that we follow isn't a straight line.