After having been through a few insurance claims in the last 10 years, I always lean toward not filing a claim. It is not just as simple as "are the repairs more than your deductible. The reasons are:
1. Just having one claim on your insurance record will cause your rates to increase on ALL your other insurance policies. The claim will not fall off your record for 7 years. I am paying higher rates on all my rental policies because when I was a newer investor I filed a claim on a $1400 repair so I would save the $400 above my $1000 deductible. That $400 savings has cost me thousands in the long run.
2. Any contractor, especially companies that specialize in insurance repair jobs, will charge more than double what you can get them to bid for just a regular cash job. And they will skillfully inflate the scope of work as far as possible to milk every possible dollar from your insurance company. It will also take much longer as they go through this process.
I save a ton of money now by having ACV insurance policies with high deductibles, and only file claims for major losses (over $10,000). You don't want to be filing small claims every other year.