Having to file a claim is never a fun event. This usually means something tragic, or at least, “not a good thing” has happened in your life.
This is exactly why you have insurance.
When determining whether or not you should file a claim, you should consider the following:
What is the cause of the incident
What is the severity of the incident
How much time & money will it take to fix this
What is my deductible
Once you know these 4 things, you can determine if filing a claim will be a benefit for you.
I always recommend consulting your Insurance Advisor anytime you are considering filing a claim.  They will be able to walk you through these steps and help you determine if you should file the claim. If you do, they will also be there to walk you through the entire claims process.