LittleDog, IMHO, RUN from this. If you are having roof problems, contact a local roofer or actually 3 roofers, and get estimates for the work.
Actually, I would contact Frank DeAngleo, he does home inspections and is very good. He will give you an independent review of your roof and whether you actually need to have any work done.
Under NO CIRCUMSTANCES sign an ASSIGNMENTS OF BENEFITS contract, which my be what the contract ment when he said he "works with" the insurance carrier.
This sounds very suspicious.
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Pennsylvania, for 60+ years, most recently, Allentown, now TV. 
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