It might look funny, but it striked in my mind. Why don't we have a gambling insurance. This means a premium to be spend every month. Through this one can be availed with two claims per year. Here the user needs to list the sites he use. When the person goes for claim, the data regarding the loss will be collected by the insurance company and provides with the insurance amount. Many won't like this, because of the privacy issues.
I don't think that's even a good type of business for the insurance companies. For sure if someone has a gambling insurance, that gambler won't be scared of losing anymore as there's a backup that he can get money again.
Even if it's just one or two claims per year, that would be a lot of money for the insurance company and they'll for sure be abused by those gamblers that would find them as a back up.
It's not just about the privacy issue but also about the insurance company itself that could go bankrupt too quick if there are too many claims.