The legal compliance piece is HUGE!

Now its a vacant piece of land surrounded by solar fields.   

For the sake of trying to learn and picking your brain, why would it be better to keep one rental and upscale the other instead of selling both and getting a significantly more expensive piece of property and trying to significantly increase cash flow?

Across all the pieces needed to come together to pull a RE transaction off: Borrower - Lender - Insurance - Title - Sometimes Broker. 

If I have one piece of advice it's buy in the best location you can afford.

Where did you go for that piece of it?

@Arron Paulino  I've posted on this many times over the last year and my advice normally falls on deaf ears. 

The biggest thing that will limit your ability to buy multiple houses a year is that thing between your ears.

Though I never put my ear to the ground as regards STR's, I plan to , and if I come up with any useful ideas for you, I'll pass them along.

A lot of CPAs get hung up on “substantial services” piece which is a semi grey area but if you understand STR the judgement calls are a lot easier.