At that point, wouldn't a standing seam metal roof be the best investment? The cost is about 3x, but beats an annual roof replacement.
And then wouldn't it be in the interest of the insurers to maintain a shared list of "bad" (unprofitable) customers and freeze them out? Which is already a bit of what credit scores are for?
"Your previous insurer dropped you, there must have been a reason."
And, yeah, when applying for a policy, the questionnaire should include "have you filed a claim for X, Y, Z in the last 2 years?" Auto insurance does this already.
Insurance companies have a privileged legal position to do all sorts of stuff.
Depending on climate there’s some other options too.
... in a non-hurricane zone, right?
Sounds like some of these coastal areas are on a ~5 year roof replacement cycle. Up here in DC, shingles last for 30+.