Do we get or we shall get insurance for travelling?

A few years ago, my father and his g/f were planning a trip. Tickets, hotel, car, etc were all prepaid. About 3 weeks before the trip, he fell ill, and his doctor recommended the trip be cancelled.

The travel agency told him, get a letter from his doctor, which he did. Everything was refunded, except $ 40.00 ( the cost of the insurance)
Now, you tell me, should you get travel insurance?

You have to buy insurance in the country in which you reside, unless you buy it at an airport before leaving on a journey.

You shall get...I command it.

But, it's a good idea to make sure you're covered...even if you don't follow my command.