We used to buy trip insurance until one time when we actually needed it on a trip to Israel. On our way back, our flight was delayed out of Tel Aviv, enough that we couldn't make our connection in NJ. We were able to get on a flight 24 hours later, so stayed over night at an airport hotel. When we got home, I made a claim with Travel Guard, and that's where the idiocy began.
First they wanted PROOF that we had purchased insurance. Our Travel Guard cards with our number on it that THEY had issued us wasn't enough. They wanted an actual receipt.
Then they wanted an official letter on airline letterhead stating WHY the plane was delayed out of Tel Aviv. Apparently the computer printout from airport in NJ giving the arrival time and our connecting departure time (and our subsequent rebooking) wasn't enough.
I was absolutely flabbergasted as to what they were asking us to provide. There was no way I could get a letter from El Al, especially considering I live on the West Coast and they fly out of the East Coast. And to ask for proof of insurance just put me over the edge.
Fortunately it was only about $100 we were out for the overnight hotel, but it taught me not to bother with trip insurance again.