Have either of you ever had to use their service?

My travel companion and I always buy the insurance offered at the time of flight booking - it's usually through Allianz. If you are booking through different airlines for departure and return, you can buy only once and easily adjust the amount of coverage later on to include your total airfare as well as non-refundable deposits. My companion recently saw a doctor in Jamaica for kidney stones. The cost was low (actually lower than the deductible) but they paid his claim anyway. I mostly buy it in case I need to alter or cancel plans due to family illness; he buys it for medical evacuation coverage since his health insurance doesn't cover it.

That being said, check every time to see about the fine print on the police - what is covered and what is not. It can vary. If you are concerned about pre-existing conditions, coverage of illness of a family member not traveling with you or other emergency situations, be sure you read definitions and scope of coverage.

If it works for you, the airline policies (or package coverage from a tour agent) are usually a very good bargain. Just read the policy before you pay the money.