When you call an insurance company and they send someone out, that means you "filed a claim". That claim counts against you, even if the insurance company doesn't pay anything out.
If the REPAIR is $1900, I'd want to know what a new roof would actually cost - might not be much more than that, which means it would make sense, to get a new roof.
When you have a $2,000 deductible, that means you pay the first $2,000 of every claim. If the claim is $1900, the insurance doesn't pay anything - but the claim still will "count" against your record, because you already filed it.
The insurance company isn't going to care who does the repair. HOWEVER. If the guy you pick, does a crappy job, they AREN'T going to guarantee his work, or pay for the roof again, until you pay to get it done RIGHT.
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