N.
K.,
The advice you've received so far is right on. I wish I had known this before I made the mistake of calling my insurance company first, rather than a roofer to get an estimate, after a storm caused a leak in our roof several years ago.
The insurance company came out, gave us an estimate for repair, said they wouldn't pay anything because it was just under our deductible amount and then informed us that if we ever make another claim on our roof, we have to provide proof that we had all the items on their list fixed or they would deduct the amount of their estimate from any additional damages in the future. Furthermore, when I tried to get quotes for cheaper home owner's insurance when we turned that house into a rental house, all the insurance companies I contacted said that claim would be on our records for 5 years and that until then, it would be cheaper to stay with our current insurer.
The same thing happened with the house we were buying. The previous owner made a claim regarding water damage to the ceiling caused by the air conditioning unit in the attic, but again, the damage was less than the deductible so the insurance didn't pay her anything for the repair. She didn't make the repair and when we tried to get home owner's insurance for the house when we bought it, her claim went against us because the claim stays with the house, not the person who owns the insurance policy. I couldn't even just tell them "yeah, it's been fixed." The other insurance companies wanted to come out and inspect the property and take pictures of where the previous damage had been reported and they wanted proof of the repairs.
The whole process is messed up if you ask me. Definitely get estimates from reputable, insured roofers FIRST! And, if it were me, I would only make a claim if it's signifcantly higher than my deductible 'cause you end up "paying" for it for the next 5 years if you ever have to make another claim, want to change your insurer or you need to sell the house.
Good luck!