I assume a "worst case" scenario eviction process and roll those costs plus a premium into my expense/rehab numbers. 

After everything was restored to it's previous state the insurance company offered me a 'freebie' to install auto shut off valve with the help of a water security company referred by them.While I did proactively follow-up with the water security company it was very challenging for both me and the water security company to find a professional who can do such specialzed work involving sensors.I spoke with the insurance broker and they told me there is not much they can do except end up paying a higher premium to the newer insurance company if my current insurance company cancels the policy.I now feel being penalized for no mistake of mine.Appreciate any advice from experienced members here.Thank you.

Maybe in financial terms but money would still have been paid on taxes and HOA so the full rent amount isnt a loss.Short-term rentals are always going to be a premium in south florida so that's unfortunately just the nature of the beast.For an older lady, any of the 55+ communities in delray are usually solid. 

I presume you may have lower vacancy but not sure if you were able to rent for a premium.

What about when the lender goes to pay the homeowner's insurance policy and notices that the premium increased substantially because it is no longer a primary residence, but a rental investment. 

However there is a stress-premium people pay as well, compared to my friends who have fourplexes and triplexes.

Don't pay a premium for that, just acquire the property.  

Also make sure they don't charge a buyers premium or if they do just be prepared to include that in your budget.

I also signed up for a free trial of the premium membership at Wealthfit.com.

My guess is they are charging a premium and you can pay someone to do it for a lot less and you'll have a say in the matter.For the $4500, I'd take them to small claims court.