Credit is a factor as bad credit may limit options, or may have the lender require you to put 10 or 20 years of taxes and insurance into escrow. 

The moral of this story is to have good home owners insurance!

Florida and Gulf Coast insurance should be a concern. 

I understand I cannot legally require them to respond, unless the notice specifically requires it, like for instance, a notice of entry, but it's making it difficult to manage the property, and I'm not sure how to proceed.

A successful rental property should offer positive cash flow, meaning your rental income should exceed your monthly expenses (mortgage, taxes, insurance, maintenance, etc.).To find the right tenants, ensure the property is priced competitively within the local rental market.

Ensure you collect a proper security deposit (typically one month's rent in Florida) to cover potential damages.Your plan to increase rent next year makes sense given rising costs (taxes, insurance, and maintenance).

Does he understand, Deeds, Due On Sale, Insurance, tax implications, servicing, contracts and so on?

Go ahead and proceed. 

Quote from @Meliisa Lee: I recommend splitting the properties or selling them off and splitting the proceeds.

Taylor sent multiple email inquiries to our insurance provider asking what risks their policy covered.