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This is a no brainer. Install the roof immediately. Don't worry about the weather. I have seen shingles installed in 10 degree temps....and they're holding up fine. Chances are excellent, that even though the roof isn't leaking.....its time for replacement. Why else would the underwriters squak?

IMHO, a trip to a lawyer will be completely counterproductive. You'll likely get charged over $1000 by the lawyer just to "look into things". Do the math.
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