I looked recently (more for Mom than myself) and although I forget the details* Allianz had annual policies in the realm of $400-500 that looked reasonable.

*The devil is in the details of course, like how much coverage etc. And how often you expect to travel per year of course.

​​​​Strictly from the standpoint of probability, all insurance is a bad "bet" -- where it provides value is peace of mind (which is a squishy emotional thing that's hard to quantify) and protection from what gamblers/mathematicians would call "risk of ruin" or bankroll considerations.

There's a school of thought that if you can't afford to write off a trip then you probably shouldn't be taking the trip at all (assuming it is a discretionary/leisure trip). I.e. not that anyone should be glad to lose that amount of money, but if the loss of it would significantly impact your finances, then taking the trip may not be a prudent choice to begin with even if you're getting something of value in exchange for the $$.

​​​​​​Viewed that way it's probably not worth paying for trip insurance for the purpose of trip cancellation (esp since cards like CSR cover that). If you are quoting for a single trip (not annual policy), Allianz lets you set the trip cost to zero, and then you're only paying for emergency medical payments/evacuation etc.

Although if that's all you want, ISTR a FT thread about different annual products and in particular something like Divers Network? Which provides surprisingly cheap annual evac or something like that. (I'd try to find the thread but not in a great place to do that at the moment)