RE: When to buy and not to buy insurance...
Thank you @crypto.piotr.
The best thing to do is have enough supplies for at least 2 to 4 weeks. And people who live within storm surge range, 20 to 40 miles from the coast (also depending on the track and intensity of the storm, plus the topography), probably should consider evacuating from the storm. In reality, people usually evacuate if they live within 10 miles of the coast. Going to a hotel or visiting family further inland is commonly what people do.
I've never made an insurance claim on storm damage, but I have made insurance claims. I used to work for an insurance company and have known many people who have filed storm related claims, and the insurance company usually did a good job in paying those claims. But people do have experience with shady companies that don't pay enough or nothing.
Usually with a major storm, like a hurricane, insurance companies pay the claims, even the shady ones, because they can't deny the hurricane did widespread damage. This picture (taken by someone else during Hurricane Harvey in 2017), which is close to where I live, says it all.
Great questions @crypto.piotr. And thanks again.