There is so many "red-flags" here I am not sure where to start..... - you state it's an "executive" townhouse.

Quote from @George Red: Interesting, maybe a "payment holiday" on next year's taxes for the amount people have paid over what they would have otherwise been required to pay  with the errant assessments.

If you do research ahead of time, what are some red flags that would cause you to back out of a deal or add a couple thousand to the deal cost for legal battles/ cash for keys?

I had an applicant years ago that got a random $10K deposit and that was a red flag to me.

Rentometer can be handy here.Vacancy Rates: High vacancy can be a red flag.

What are some red flags?

This could save thousands, but might add so much red tape that it may not be worth. 

Do you think this storm will cause prices to finally decline in the once red hot short-term rental market in Florida?

I am worried that my property expenses will leave me in the red because of the current costly housing market.

Do you prefer to have an open "application period" to collect applications and then make a decision based on the "most qualified" or do you take the first qualified, even if on a personal level they put off some red flags.