The three criteria for a security are: 1) An investment of money, 2) where the investor is expecting a profit, 3) from the efforts of a third-party.

As I wait for my third party to complete the screenings, I am thinking ahead to how I will make my selection.

So in January you will probably have about a third of the nightly rate than you do in July (Florida numbers, but probably somewhat applicable).Maybe you can look at other similar properties online on Airbnb/VRBO and see how occupied they are and what they are charging nightly and seasonally.

The third factor is access to good contractors. 

Just not sure if DBA offers enough protection - I'm leaning towards DBA for the first deal and then worry about creating the LLC once I expand to second, third... deals 

I am not exactly sure how the insurance and tax payments would work.I realize with a deed of trust it's really easy to have any number of third party note servicers hold escrow, and ensure insurance and taxes are paid. 

It is a pier and beam house with two supports on a cement porch and the third post is on a leaning pored cement block approximately 12”x12”.

More often than not, the upstairs was not originally finished... then decades ago someone finished it into a third bedroom.

It may be a criminal offense for a director of the HOA to provide debt status information that’s not public record to a third party, or it may open up a civil liability issue, or it may violate terms of the HOAs errors and omissions policy.

I'll be honest: I didn't even read past your third sentence.