I didn't when I was younger. We started buying it a few years ago. I used to think nothing would stop me from taking this trip. Then I realized there's a lot of things. Once we started cruising, paying in full a few months in advance, got me thinking about it. Another cruise I slipped and twisted my knee as I climbed back into a boat on an excursion. I wasn't seriously hurt but if I had been it could be expensive to treat, not to mention the rest of our cruise ruined. Insurance would cover not only the medical costs but trip interruption too.
My TA said if people need emergency medical evacuation off a ship, it can bankrupt a family. I got to thinking about dh's family history of heart disease and decided I just need peace of mind. So now I buy it on all cruises and very expensive trips, as pp mentioned an Alaskan cruise. Not for our typical Disney trips since they are usually short these days.
Last year we were doing a 2 nt stay at WDW then a 3 nt cruise. "Cheap" by
DCL standards so I didn't bother with ins. Didn't a tree fall on our house the morning after we arrived! We flew down after school, went to bed woke up and went to our ADR at Ohana and that's when we got the call from our neighbor. Once we saw pics we knew we could not cruise with our house like that and just ignore it. Plus ds19 (not with us) having to evacuate to my parents.
We were so relieved we hadnt yet boarded the ship.
Anyway, turned out to be a very expensive breakfast with Mickey.
Right before another cruise, my MIL had a heart attack the day we were due to fly (1 day before the cruise).
Now I buy it every single time.