Lots of broken hearts and destroyed finances over situations you describe.

If he works per hour, he might agree to work for a day/two and then allow you to decide if you want to continue.If you know you won't have the heart to 'fire' him if he does not know how to do the work well, decide before hiring him if your willing to take that risk.

What about a heart attack or stroke.

A couple of the tenants simply left with cash in pocket (and only paid once they leave the property, a common mistake made by good hearted investors).

He is an older gentleman and a veteran who has had multiple heart attacks and is in the process of filing for disability. 

Those who lack determination and self motivation need to do something else as this business is not for the weak hearted. 

I'd use him again in a heart beat.

The only reason I am hung up on this property is because the interior is very nice, and the location is quite convenient (right across the street from the medical district which is the heart and soul of my community).

I am looking to put my heart and soul into making whatever property I buy into a place where people want to live and that I can house hack until eventually refinancing and expanding my portfolio.

There isn't even a thought or decision here... had they come to you with a heart tugging humanizing story at least there is a chance you might consider especially if you feel the circumstances extraordinary, or be upfront and honest about whatever hardship they are facing and perhaps you have a solution that works for everyone - but a threat?