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.

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.  

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.

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? 

I've tried many different strategies, and all have turned out average...economy of scale and systems & processes play a key role in long-term success.

You get blocked by carriers then expect your personal phones to be shut down.You don't have to using a service like Launch Control or the others...Only with the google play app do you have to use a personal phone number and I haven't used that number in 1 1/2 year.The anti spam things the networks are doing are pretty difficult to get around I can see why that SMS platform threw in the towel and has you using your real phone number.