So. We buy travel insurance for every trip. Even land-based trips. (not weekend getaways, etc. You know what I mean.) So lets see... over 20 years, we've probably taken 20 trips with Insurance. Out of those 20 trips, we have needed it twice. Once for a cruise vacation, one for a land-based vacation.
The land-based vacation was for a trip to OBX and a hurricane wreaked havoc on the barrier island and the island was still under evacuation orders the day we were to arrive. And, the house was damaged and so we couldn't even salvage part of the two-weeks. We had to provide all sorts of documentation (including the public evacuation order and documentation form the rental company that we could not get into the house and they had no other comparable house to place us) but eventually we received a check for all of the expenses related to our 'loss'. I want to say it took about 6 weeks.
The cruise vacation, our primary residence was damaged during a hurricane that came through two days before we were to board and we could not leave because our homeowner's insurance requires that we do all we can to protect the home and property until they could properly come out and assess, etc. so we missed our cruise. Again, lots of documentation including my insurance binder stating that it was our responsibility to secure our home (which took a while since we had multiple egresses damaged) and there was some other kooky thing they asked for but I can't remember what it was but my husband got it and sent it off. I think we got that check within 2-3 weeks that time.
We always get 'cancel for any reason' insurance and purchase it immediately after booking (we consider the expense part of our 'deposit') as the whole per-existing condition thing is a big deal. And insurance companies are slick... if you have to cancel your vacay because your mother is on her deathbed and you didn't get insurance that covers per-existing conditions? They can say HER per-existing condition isn't a covered reason to cancel. In other words, you should just big poor Mom farewell and your butt on that plane/ship. And really, just about all of us have parents with some sport of per-existing condition...
ETA: My mother just reminded me about the time I broke my ankle on my Celebrity cruise 14 years ago and had to get immediate medical attention while in Hawaii and all of that was covered by my insurance. So technically, that makes three out of about 20.