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?

I am very transparent and will answer any questions you have.

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

Looking to create a transparent system between us so it’s all out on the table!

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