Only for trips outside of the United States, since most health insurance policies do not provide coverage out of country. An accident or unexpected illness might create a financial burden in addition to all of the other problems. Luckily, I have never had to file a claim. We are planning a trip to Italy in September and I will buy a travel health policy.
I have bought travel insurance a few times and it has paid off more than once. The first time, we booked a Disney cruise back when Disney contracted out with The Big Red Boat. Notably, we did NOT buy insurance from the Big Red Boat but from a third party company. Two months before we were to set sail, the Big Red Boat was slapped with Bankruptcy orders on all of its boats. They were stopped in Nassau; we got a full refund and would not have gotten that refund from the bankrupt Big Red Boat travel insurance. My advice is that as long as you have kids or elderly guests who might get sick at the last minute or are spending a good chunk of money, get the insurance.