Mine is a single story concrete block house built in 1962. It sits atop a dune ridge. The 2 car garage is the only thing at street level and the entire lot sits way above sea level.
In all the years I was forced to have homeowner's insurance, not once did I have a claim because through the years it never sustained any damage, despite numerous storms over the years that ripped through the area.
I made a business decision when my mortgage was paid off 10 years ago to go the self-insured route. In the past 10 years I've saved enough $ to pay for a new roof 3 years ago plus a ton of $ left over for future structural maintenance & improvements, as I wish to make.
The straw that broke the back for me was when the insurance company said I had to replace my roof because it reached a certain age. Even though my roof still had several years left in it - THEY wanted a new one - at my expense. I said no way and exercised my options.
Lastly.....worse case scenario....in my case, the property is worth WAY more than the structure on it due to it's proximity on the barrier island to the ocean and ICW, so I could always sell my lot if push came to shove and make a boat load of money to go live somewhere else.
So the decision will be different for everyone. As it was for me.
