My family is extremely hard to deal with and cannot leave emotions out of business.

Buy based on the numbers, not emotion and you'll come out ahead in the long run.Cheers,

Happens a lot here in Cleveland, especially the more run down parts of town.These sellers are often in a tight financial position and make emotionally fueled decision.

Any underwriter is going to plug in multiple numbers and factors but one of the biggest ones that are commonly overlooked especially in the terms of a community bank or smaller Bank is the emotional evaluation.

Last thing I'd want is for the existing system to fail, a sewage backup to occur, and have to worry about providing temporary housing for a tenant while a costly hazardous waste cleanup goes underway.  

You are happy with owning the property and are looking to justify that emotion.

Try less emotional connection to the subject matter. 

I have other opportunity so I'm not emotionally attached to this deal so that gives me the upper hand.

Stop thinking emotionally and move into critical thinking.

I realize that my logic of him having a 0% return annually by not investing with me versus an 8% or higher return + good real estate experience is irrelevant because people are emotional.