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Guess I don't understand why the insurance company cares about the condtion of the roof...perhaps in case they would be paying for water damage in the near future ?? Anyways...a few years back we had the roof and siding replaced in the "dead" of winter...the coldest January in years and everything seems fine. Don't think the weather would be a problem. We do have the "locking" shingles on our roof because of where we live a nd the blowing of the winds. Sounds like a train sometimes it blows so badly. But if I had to do it over again I would go with a metal roof. Good Luck !!!
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