My guess is your lender just wants someone experienced with insurance.

If during the screening a applicant gives any push back or questions my lease I reject them based on attitude.Once I narrows it down to the best I have a second personal interview to insure I have made the right choice before accepting them as a tenant.I reject any applicant I believe will be a bad personality fit for my property regardless of how qualified they may be.

When I evaluate what I can pay it is based on gross rent minus taxes,insurance, mortgage payment, cap ex, maintenance and vacancy.

I assume by mortgage you're including PITI (Principal, Interest, Taxes, and Insurance)? 

I was remodeling the entire kitchen, insurance paid for a lot of that, and I knew that the droopy tile would make the kitchen look not as good as it should have. 

(All pools are usable etc.)What are the typical costs of utilities, property taxes, insurance and the cost of furnishing the property in a manner consistent with the rules?

As a reminder for any other readers, the 50% rule applies to gross rents and accounts for all expenses like management fees, taxes, insurance, vacancy, maintenance, Capex, utilities, water, legal, yard, etc..You should only use the 50% rule for a quick analysis and a true historical picture of expenses on a property is preferred.

Insurance costs vary widely in the Keys depending on location and type of construction.

As landlord, I didn't have any additional insurance. 

Hopefully her insurance allowed for some forced appreciation through new renovations.