... I brought in my insurance company. I had actually been saving ads for roofing companies that offered free inspections, because I wanted to know what several thought. Then a guy comes to my door, doing the same thing yours did, but my guy was in his 30s and had material about their company, its BBB rating, reviews, history, etc. He offered to have his roofer do a free inspection. Their roofer is late 20s, said we had hail damage and showed me photos he took (and it was pretty clear we had damage; the metal vents were badly pitted). So I called my insurance company and asked them to look. They sent out their guy, he walked the roof with the roofer who had been here earlier, and said yep, you need a new roof. They have already done an estimate and cut me the first check. Now I just need be sure the roofer is good and the work is done right. But the whole thing makes my spidey sense go off.