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Why would it only cost 15$ per square more for extra layers?It is the same, if not more work than the first layer. It is usually much more brittle and disposal fees are the same. Each layer would cost as much as the first one on my jobs, minus setup and drive time. I agree the money he wants is excessive and it may even be entirely his mistake depending on how well hidden it was.
Don’t believe everything you read on line, especially Angie’s List. The highest rated roofers on there in our area are usually the biggest hacks, but cheap.
Or have had the most friends and family write fake reviews, hell you can buy reviews for that matter.
I charge more for additional layers than the first layer, for all the reasons you listed.
People that suggest that additional layers is no big deal are salesmen.