One thing you might run into is the “three tab vs four tab” shingles. Apparently the building codes now require four tab shingles. If you have an older roof with three tab shingles it cannot be repaired. I agree with the other responders, it sounds like you have an a roof that has reached the end of its life span.The insurance company will not pay and you will be hard press to find a company that will insure you with the current condition of your roof.
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The difference between genius and stupidity is genius has its limits - Albert Einstein
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