I've had several bids, all much higher than the original, unrealistically low contract price, with of course a lot of variety in the price, experience, and track record of various builders.

From years of investing in Florida I have often heard that they are very difficult to work with when you need to enter a claim.

Recent survey claimed 73% of millionaires either own it or wanted to own it.

Your proposed strategy may make litigation after a claim arises more complicated and costly for you to defend.  

We had a roof damaged in a hail storm and got it replaced and paid (minus deductible) via an insurance claim. 

A higher deductible for a lower premium might be good if you are diligent about saving that money to have available in case of a claim.

This approach avoids any specific mention of what you found and keeps the denial grounded in general terms, which helps minimize the chance of confrontation or claims of discrimination.3.

A majority of this hurricane's destruction was flooding (flood insurance claims) so do not expect wind insurance to jump so much. 

I also currently have a personal umbrella policy, but they are claiming the personal umbrella wont help liability in the event an STR guest wants to sue.

Communication is always key.Even if things aren't going as planned.Granted, I have also witnessed many unrealistic expectations and got blasted for "communicating" every nut and bolt to an investor.So it can be a fine line