I would have gone on the roof with them because you don’t know if this sales guy actually damaged the shingles before taking the pics. I would then hire a good home inspector or another roofer to check the roof out before doing anything.
I would also contact the state and maybe get them to do a sting operation with these guys to put these guys away.
If I needed a new roof, I would work with both my insurance company and the roofer, never sign any rights to a roofer and his lawyer, and just handle it myself. The roofer would have to be licensed and bonded, carry insurance for his employees in case something happened.
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