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First, conduct a visual inspection from the ground using a pair of binoculars. Check every inch and try to cover every angle. Look for signs of aging such as cracking, curling, or loose shingles. Pay special attention to the valleys, vent pipes, and all spots that break or meet the roof. The flashing and boots should be intact, undamaged, and in their proper places. Likewise, the edge should be flat with no signs of wind damage.
You will also need to climb into the attic to check the condition of the wood parts, such as trusses and the underside of the deck, if visible and not covered by foam insulation. There should be no water stains or signs of warping. Check the foam or blown-in insulation for clumps, which are a sure sign of water damage.