I think it helps to have a candid elephant in the room conversation with the tenant, that way, if you choose to part ways, its in the most human(not humane) way possible. 

The lowest form of manipulation that any human can use against another.

If you like this man as a human and want to help him out, explore seller financing options that could be a win-win situation.

Be as "human" as possible and say that you're in a really difficult place (as he well knows) and need to go a different direction. 

Humans in general are forgetful and your mind is much more focused on preserving your property than even your best tenant. 

If the tenants are basically good human beings and want to get along and have a nice place to live they tend to get along better in a multi family environment.

Meaning, for every homeowner who is under insured by 5% (remember, that valuation is subjectively determined and subject to change depending on a contractor's skill...etc) there will be one who is 5% over insured (again subjective and subject to non-robotic human craftsman, and variables).But, that is why carriers use the 3rd party rating systems mentioned in your posted article.  

There is always a human factor and sometimes things don't go your way despite all the preparation and due diligence.

(Im doing Home Depot demos and Habitat for Humanity to get hands on experience in fixes to homes)Any help will be greatly appreciated thank you so much!

Housing is a human right and you should not profit off it.3) If it wasn't for landlords buying up all the properties and pushing prices higher, I'd be able to buy my own home.