I've never bought insurance, and I'm not sure that I've had but a very small handful of times I would have had a claim.

I had a suitcase run over by a tractor once, but most of the contents survived and AA replaced the suitcase.

I've had a couple of suitcases misdirected but never for so long that I would have even bothered to go buy new clothes.

I've had maybe two times I got stuck overnight due to Wx and had to pay for a hotel, and I remember 3 times I had a flight cancelled and I needed to get to my destination badly enough that I rented a car and drove (2 1/2 hours, 5 hours, and 9 hours respectively).

I also was responsible for pricing and other tasks on "supplemental" insurance programs. The commissions paid were usually in the range of 35%. Which tells you how much profit is built into these things.

I imagine that if I had a severe illness on an overseas trip and required medical evacuation I'd wish I had insurance, but that's all I can think of.