I find it difficult to believe that insurance companies are so stupid that they will spend thousands of dollars to replace a 20 year old roof. I would not hire any roofer who shows up offering a free inspection, and I would not allow any contractor to deal directly with my insurance company. If I thought my roof was damaged by a weather event, I would file a claim. And, if the claim was rejected, I may ask a reputable roofer for a second opinion. But, I would always deal directly with the insurance company.
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