I totally understand what you are saying. Insurance is expensive and a pain and I would rather not have to use it and nobody wants it until they really need it.
When we were younger we would take 2 or more scuba trips a year and never bothered with DAN or travel insurance. Now we take one 2-week dive trip a year and we always supplement our DAN with travel insurance.
We've had a few losses over the years and we always just absorbed them; a camera was flooded and another was lost, and we had some brushes with hurricanes and had to make sudden trip changes and incurred penalties and lost deposits. We've also had a few medical issues, including a ruptured ear drum and a case of bronchitis.
Some of insurance plans we looked at had qualifying conditions about trip cancellations. Like you have to buy the insurance within a week of booking the trip; or if a disaster strikes the area but the airport has re-opened and your hotel is still standing then they won't cover the cancellation. Or they won't cover a cancellation unless the State Department issues a traveler's advisory.
Years ago, we actually bought some expensive trip cancellation insurance and tried to use it but were denied. We had planned a major trip to Egypt, including a stay in Sharm el Sheik, a week long liveaboard trip, and then time in Cairo and other areas visiting the historical sites. Unfortunately the date of our trip was about a month after 911. All US air travel was cancelled for a period and there was a lot of fear everywhere and we were worried about being Americans traveling to the Middle East. But the State Department hadn't issued a traveler's advisory, we were not at war with Egypt, and there had been no natural disasters, so if we cancelled we would have been out the full price of the airfare, the liveaboard trip, and some other deposits.
We decided to go on the Egypt trip and I am glad that we did, we were in no danger and it was a wonderful and unforgettable experience; but it really soured me for a long time on the idea of trip cancellation insurance.
I didn't seriously start looking into trip insurance again until our frail elderly parents started getting very ill. They have all passed away now but there was a period of several years where one of more of them was very sick and in/out of the hospital just when we were leaving on vacation. We have siblings at home but we were a bit afraid to leave the country only to get bad news and have to rush home. I started looking into cancellation insurance and a lot of them had conditions that would be difficult to fulfill. Like "Did the family member develop the illness after you booked the trip? If not then you are not covered." Since our parent were afflicted with multiple chronic conditions that could turn life-threatening suddenly we wouldn't be able to qualify.
That's why we eventually decided to go with the Travel Guard coverage that includes "cancellation for any reason" as well as medical and property coverage that was recommended by our Travel Agent; we also buy the DAN Preferred coverage. And now that we are older and we are starting to develop our own chronic health issues; it just makes sense for us to have travel health coverage in addition to trip cancellation.
For someone that takes a lot of trips, I am sure that some insurance firms must provide year-long travel coverage because corporations buy it for their employees that travel on business.
We probably pay too much for insurance (and hope that we never have to use it!) but having it seems like a good idea to me after considering what could happen and the risks of not having insurance. But everybody has to make the decision that seems best to them. It took me awhile to decide to go with insurance so I'm glad that it was never a big issue for us.
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