So far find a contractor that is reliable and responds to you.

Question 2) If a broker's license is required for regularly handling scheduling and payment, would the first method be a possible solution that doesn't require a broker's license?

Clearly, like Mike pointed out, your attempted solution of equating your reputational risk with his monetary risk didn't pan out. 

I will look into what a SDIRA (Self-directed IRA) is, I haven't heard of this option.If I don't find a solution to my post at the very least I am  learning a lot  about retirement funds and the rules around them.

Perhaps a fee-only financial planner is the solution to this particular problem?

That seems like a clean cut solution to me. managing it is another thing  you would have to deal with and that also seems like a long shot, especially with the short term rental options. 

Need a reliable contractor looking to update a condo rental on Siesta Key. 2br 2bath.

A very simple solution. 

To get the most reliable information I recommend visiting city hall to access deed and tax records. 

When vetting your PMs, ask the questions that might provide solutions to these problems.