Hudson Valley winters are hard on roofs: snow, ice along the eaves and freeze-thaw cycles lift shingles and open leaks. A stain on an interior ceiling is rarely right under the leak, because water runs along the framing.
Many New York municipalities require a permit to replace a roof, and the building code limits how many shingle layers can build up: generally, a new layer can't go over two existing ones. Ask the contractor whether your job needs a permit in your town.
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