He had insurance on the S-Corp for one million and none for himself.

Maybe it has more to do with the software than the company (although their customer service sucks), in which case you might run into the same issues with other emulators, but it has just been constant headaches.

Insurance cost for weather-related disasters is growing to a major concern in many of the southern markets.

Anyone speaking in "sure-thing / simple" terms, I call BS. 

We owe $154k on the property and the interest rate is 4.25%, the monthly mortgage is $1050 with taxes and insurance.

They now use "Dave" to handle customer inquiries efficiently and promptly. 

Those can indicate poor management, deferred maintenance, difficult and expensive upkeep like ocean front which will bring up issues with rising oceans, insurance, and hurricanes. 

I'm unsure if I would use property management at this point, and there would be some insurance.  

Yes, you can deduct related expenses including gas, loan interest, insurance, etc. using the actual vehicle expenses method to deduct auto expenses for your rental or other businesses. 

Taxes have to be paid, so does insurance, what about maintenance?