Your proactive approach—especially the hurricane-proof renovations—really positions you well in terms of asset protection and long-term value.

Don't fall for this @Laura Higgs Whole life insurance is designed to leave money to your heirs and is not a funding vehicle for real estate or an "infinite bank" Here is a post with more detail https://www.biggerpockets.com/forums/519/topics/1231319-how-smart-investors-use-life-insurance-to-build-and-protect-wealth#post_6978183

FL seems to have reigned in HOAs recently, so who knows what they are allowed to do.I know that in CA, an HOA can ban smoking in units because smoking is not a protected class and the HOA has an interest in the safety & health of the building. 

If things go wrong, you have no protection.

I have better luck with posting in the zillow rental section;   rent before you buy, live in a great property while you get yourself ready to finance a great home....Our business model;   protect the buyer or tenant at even our own expense. 

Lenders that don’t require an appraisal will perform a desktop appraisal but will typically have a very conservative view on the value of the property to protect the company’s investment.

Any other ideas on how to ensure our funds are protected? 

Very conservative approach that protects the seller.There is a long thread that covers what I'm talking about atPace Morby Mentorshiphttps://www.biggerpockets.com/forums/79/topics/1001612-pace-...  

Also keep in mind that many of these vacation locations have began changing enforcement and regulations for STRs so make sure to research a lot about pending legal actions and public sentiment of STRs in any market you want to enter and formulate several exit strategies to protect yourself in case there is a shift in the market there.

In fact one of the themes of my posts is dissuading investors from over spending on entities and asset protection.