Without writing a book, google these two terms.Zombie CondoHOA Special AssessmentThen search for news on condos in Florida from this year.

Eric, First, Good idea on searching for a realtor specializing in STRs.

Here's the bigger lesson I learned: If a tenant asks for special considerations, or reduction of fees - those are ALWAYS the ones who are the problem tenants.  

I am the VP of OmniKey Realty LLC and we specialize in working with investors to grow their real estate portfolio.

I think what you’re referring to is a checkbook IRA so you can bypass the custodian when performing transactions/investing and all assets/accounts will be held in the name of a special purpose LLC or Trust which is the instrument that gives you checkbook control.  

A special committee was formed last year, and was to hold 6 non-public meetings and then send their finalized recommendations to the commissioners in November.

I am expanding to more specialized Airbnb this year.

You want to find a lender for this that specializes in STR financing!

It speaks to "nothing special here", that's what it conveys. 

Connect with a local architect who specializes in new construction duplexes and get their feedback on the highest and best use of the land, as is.