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.

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. 

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

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.

He claimed that the market had changed since the fall of 2023 and that he could no longer go through with the original deal unless we reduced the assignment fee by $15,000.

There will be an influx of workers to help repair the area and adjusters for all those file claims that will need short term housing.