How likely is it for insurance to cover the replacement or repair of a 20-year-old roof?
In my experience working as an insurance broker, I would give you this genuine advice:
How much money you get for your damaged roof depends on your insurance plan.
If you want insurance to cover your 20 year old roof, then consider a cover that is based on RCV terms. RCV simply means replacement cost value, that is the insurance will pay you the entire cost to replace your roof with a new one, no matter how old your old roof was. However, if you had insured under ACV which is the actual cash value, then the insurance will pay you for the current worth of your roof, which isn’t much if it’s old. And for a 20 year old roof, you wouldn’t fetch enough money to fix your roof.
Some insurance companies will not provide coverage on a 20-year-old roof. If they do, your roof may have to pass an inspection before renewing the policy. If your roof reached the 20-year mark with no problems, you got the ROI expected from a quality installation.