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I wish insurance was more flexible with risk and deductibles, 20 year old roof, your deductible is 20000, 5 year old roof your deductible is 500, something that equalizes the risk without the need to drop customers. Heck I would self insure or set an extremely high deductible for rebuilding, but I still need coverage for any liability risk like when the mailman trips on my sidewalk.

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That's only possible when the regulatory environment allows it. If your insurance regulators won't allow that kind of flexibility, then they have to look for other options.

This is often approached through the lens of consumer protection. As a result, making thing flexible to allow insurance companies to say "Hey, you really need a new roof, but if you choose not to here's the price of that risk" is not prioritized. Approving rate increases is.

You can get basic liability coverage if that’s what you desire. But be prepared to pay out of your pocket in case of total loss. If you have a mortgage you’re almost certainly required to hold coverage.

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