You are betting on the business doing well, so a lot more goes into screening prospective tenants. 

And you can bet there will be many that feel the same way.I flew to Maui 8 months after 9/11 and tourism numbers were still very low and hotels were significantly affected.  

That's your best bet for finding locals who know the area.

I spent 10 weeks doing these gaaadamn boring agent classes to bet my license, and then after some research and a LOT of complaints from investors turned agents, they regretted getting their licenses.Legal or not?

Something I did not mention in the original post was setting up a lease, my guess is that the best bet is to find a boiler plate for the state you reside and then consult with a lawyer to custom fit it to your needs?

Video walk through is your best bet.

Each night I would enter into each column what I spent/earned each day and most importantly, what I spent it on.

I would put bets on it being one or more of the first three, versus the fourth. 

Now that I'm more experienced and cashflow is less important, I may take a deal that has zero cashflow and bet more on appreciation, but only after accounting for all expenses, including setting aside money for capex or vacancy.Here's a guide that describes what good cash flow looks like and how to analyze a property.https://www.biggerpockets.com/...

I just know it's a safe bet with growing population, good taxes, good schools, fair laws.