Here is my brief experience with aircraft insurance on a personal airplane (as opposed to my experience as a chief pilot/manager of a corporate flight department):
I suffered hangar rash on my right wing leading edge on the way to the 2002 Las Vegas convention due to some unknown person who manipulated my tie-down ropes in my absence. The repair estimates ran between $7K-$9K and I was insured with A——- and carried a $1K deductible. I filed a claim but dragged my heels on the repair because I didn’t have the time to do without my plane and did not have a shop I trusted to do the required entire leading edge replacement.
The claim went “cold” and after 5 years I became acquainted with Del Lehman of Mountain Airframe, a person whose workmanship met my standards and when I contacted A——- (ins. Co) was told the “cold” claim had been closed but I could re-open it. So I did...Del fixed it by (instead of replacing the entire leading edge) installing my right-wing land/taxi lighting as a mirror-image of my left for about half the prior estimates. A——- insurance agreed to pay the entire amount since I was willing to accept a less-than-full claim amount ($7-9K). I am very happy with that solution.
Some years later I became unhappy with A——-’s “family exclusion” (one of the major reasons their premiums are somewhat less than other underwriters) and changed to F——- insurance co. (who insured the corporate jets I flew while on furlough from my regular job) because they offered attractive coverage at very attractive premiums.
Recently I have been receiving invitations from A——- to return to them.
Very recently I visited with one of our Members (a retired SWA pilot) who told me of his experience with insurance on his 170: Since he’s turned 75 he has found that almost no one will insure him AT ALL despite his perfect flying record and Zero claim history. His insurance is with A——- now because his previous agent, F——-, has dropped him due to age.

He advises me to consider the possibility that it might be beneficial to find insurance which will insure older pilots as not all will do so anymore (he says virtually NONE will insure past age Eighty...EXCEPT A——- who apparently does not discriminate against age)...and the market is becoming even tighter as the market shrinks. He is recommending A——-. Hmmmnn.....