I think FFB's Dads point is that if people would not abuse Insurance claims (does not sound so in his case), like faking auto injuries, thefts and all the other nonsense people pull on insurance companies for a free ride, then all of our insuance costs would be half as much less or more then they currently are. Kudos to your Dad, but he needs to file a claim. It's legit and will not fix the root problem by not doing so.
It seems obvious to me that your dad should use his insurance coverage. If I had a significant dent in my car that "i had to fix anyways" before getting my car totaled by another driver, I'm still going to use my insurance on the car. Sure your Dad's roof was damaged, but unless the hurricane had extremely minimal effect on the overall condition of his roof he should file the claim.
That still seems pretty steep. I had 6 layers on my roof that was stripped off and it didn't costs anywhere near that.
Your dad may be getting ripped off because roofers are so busy right now. Since he's paying out of pocket, if they since he's got money they'll probably highball him. They can't do that with the insurance companies, because the check is what the check is. Also, it doesn't matter what shape the roof is in, he's paying for insurance on it. It's the insurance company's burden to go out and see what they're insuring and to set premiums accordingly. Just because it was an old roof doesn't mean the insurance company shouldn't pay to replace it. That's what he's paying for!
No it's not. Its the insured's burden to report, accurately, what it is they want insured. And besides, a carrier would never insure a roof for more than the standard cost to replace it (i.e. in this case, they would owe to remove one layer, not 4 or 5). Fatty. Unless your dad is afraid of rate increases, there is no reason not to report it if it was legitimately damaged during the storm. They probably won't pay all of it, since there are several layers, but at least he'll get something.