I always advise at least giving it a shot with insurance before committing to paying out of pocket. You would be surprised to what I've seen bought, all depends on what insurance company you have and how the field adjuster is feeling that day. You don't need a roofer present for the adjuster meeting and it typically will not affect your policy if you file a claim and it is denied. Again, I can pull a hail report for you if you would like. Its free and I promise I'm not trying to sell you a roof, I'm booked months out right now. It will tell you what wind/hail events you have had at your address for the last 10 years