It seems not much different than any other type of insurance.
Insurance companies are businesses. All forms of insurance are profitable, or they wouldn't be offered (or the prices would be raised until they were profitable again). In other words, over the long run, buying insurance is always a losing proposition from a strictly dollars-and-cents point of view. With that said, some expenses are so large that it makes sense to get insurance to protect against them. Things like your house, your health, and your car. My philosophy has always been to only insure the things I couldn't afford to replace out-of-pocket should something happen to them. A $20,000 car? Sure. A $200 XBox? No. If you're playing in fantasy leagues where the buy-in is so high that you can't afford not to win, then I'd say the problem isn't that you don't have fantasy insurance (holy double double-negative, Batman!).In my mind, buying fantasy insurance is a lot like going to a roulette wheel and putting money on both red and black. Sure, it'll heavily mitigate your losses... but the fact remains that over the long run it's a guaranteed losing strategy (whereas every other bet is just a
likely losing strategy)