The cherry on top is that he is always enthusiastic, and he truly seems to thrive off of helping and coaching others which is infectious. 

but with that said, it seems like you're assuming OP will be able to have a high performing / top performing STR (which i think we would all agree would beat unleveraged market returns.) 

You’re thinking through things the right way, and Detroit can be a fantastic place to execute your plan if you get the right setup in place.

(With invested capital, this matters, plenty of people are worth "taking a shot on" in other capacities, just not with respect to managing my money).2) "Is this investment where I'm giving you money the top priority in your professional life?" 

There are many STRs that do quite well in the suburbs of major cityies Off the top of my head, I can think of one of the STRs we manage that is 40 mins outside of Dallas and it has a great occupancy rate.

In tip top shape both in the mechanical systems, design, and upkeep2.

On top your due process, my advise is to trust your gut when vetting tenants.

He was at the heart (and brain) of a fantastic educational operation – one that was undervalued because he did not charge much for it.

If they can't even market themselves to be a top agent, then they don't know how to market your home either. 

If they have, you extend that time to 6 months from date of death.On top of that, every month you delay buying the house, the loan balance is going to increase.