Sure the million dollar suburbs are nice if you have that kind of money and are playing the larger appreciation game but dollar for dollar pound for pound when it comes down to rent to value ratio its difficult to find the same kind of cash on cash returns section 8 rental properties offer in Detroit.

I'm trying to wrap my head around working with investment capital long term, and there's also the potential for some seller financing from the building owners, and my cousin is on the board of a bank which could also come into play.

In your situation the OA is going to play a more substantial role because you have a partner.

I'd be interested to hear how you approach evaluating a borrower’s past performance and how that plays into your final lending decision.

In your situation, it sounds like the primary focus for you is more a quality of life play (reducing your commute time), and the STR may allow you to break even cash flow wise? 

You are WAY too eager to leave your job for investing when investing takes years to deliver a return comparable to your job unless you have a bank vault of money to play with.

There's a price/rent lag because leases are typically for a year so there's the delayed effect of old leases playing out before upward pressure on rents does it's thing.With that said, there's also your ability to refinance out of that rate and improve the rentability of it that way.

Having two solid paid off investments is more than enough, and I'd argue that it is even a better play for most people than continuing to scale and scale for the sake of scaling.  

For rental property owners, the court will pay particular attention to the total net income of your rental.So, how is rental income calculated, and how does that play into child support payments? 

You could consider house hacking to reduce out of pocket expenses.It’s definitely an appreciation play not a cash flow play but with the federal government here appreciation is consistent - you won’t get super high appreciation like some places but also don’t get high depreciation as well.