I agree with Don that acquiring an interest in property without a title policy is short sighted. 

It just seems like there will be many that fail to file their report and I just can't see the government really going after tiny businesses for so much money for something that is so easy to forget to do.

I have been able to find companies that will cover real estate portfolios on one policy in other markets but no luck in the Florida market.

The tax sale "launders" off all liens except local government liens--sewer, grass cutting, demolition. 

Flood insurance: I’m all for being conservative on insurance policies.

But if you decided to do your own thing, then ask for help afterwords, they would refer you to an attorney that handles this type of problem in your area A lot of the government back loans such as FHA and VA is not available for title insurance if you buy them Sub2.

An inland marine insurance policy for the equipment . 

The best approach is for the HOA to review their insurance policies to see if they have this coverage.

Having  more flexible cancellation policies, having good reviews, offering discounts, updating listings periodically, not cancelling on people, etc

Akin to the rest of American society.You could start with our Government.