Quote from @Paul Novak: I am curious how other people have come to determine when enough is enough on purchasing more real estate and if/when to pay off their properties?

You have a poverty mentality and are trying to do things on the "free" without knowledge.

Yessir, those both make sense that they both have a high failure rate, wholesale seems made out to be the all in one easy way to get started, but I'm not in this for a get rich quick type of mentality.

Especially the first time something bad happens (and something bad will happen) such as an eviction, slap leak, collapsed sewer run, new roof, etc it could be challenging to see the positive of having a cash negative rental.Make sure you are mentally prepared to supplement this property for potentially years through some difficult events.good luck

The home environment has gotten really stressful, so I’m feeling a lot of pressure to move out for my own mental wellbeing.

We embrace S8 applicants, but screen them just like any other applicant.Many have an entitlement mentality and try to leverage their S8 voucher by pretending to be helpless:1) A percentage won't apply because they expect a landlord to waive application fees for them.2) Many cry broke and expect a landlord NOT to charge them a security deposit.3) Many of those same S8 tenants trying to avoid paying a security deposit, won't make an effort to call the list of nonprofits we send them that will pay their security deposit if they apply.4) A lot of them try to avoid paying for utilities.

In the process you learn that the seller is under her sisters care because of mental issues.

About a year ago, I made some mistakes that led me to prison, but that experience completely changed my mindset and made me determined to rebuild my life with purpose and integrity.

This has been an extremely stressful situation as a first time landlord and I am trying to best prepare myself for what the next couple months may look like for me financially, mentally, and emotionally. 

I don’t do the mental gymnastics of inflating cash flow in my mind on a property that I put a large amount down or paid cash for.