A couple things at play here: many homeowners want to save a buck, and many roofing companies want to make a buck. That combination generally works out deals so the deductible "disappears". I can't remember how many of my neighbors said, "My roofer worked it out so I didn't have to pay the deductible!" My guess is the roofer padded whatever quote he came up with, and then subtracted the deductible to make it look like the homeowner got a break. The roofing company I used didn't work that way - they gave me a quote without looking at the insurance claim or asking about my deductible, I turned it in to my insurance company. It was higher than what the insurance company originally was going to cover, but within reason for the zip-code/neighborhood and had good explanations as to why. Part of the cost difference was that the original insurance estimate did not include some ice/water protections that local code requires, part of it was the "waste" calculations on how many scrap shingles would be left over, I can't remember the others. Insurance company matched it, I DID pay my deductible, and I got a new roof. The other two companies I talked to asked up front how much the insurance company was going to cover, and was then willing to "work the numbers" for me.
