Yes, this one is a serious can of worms to be opening. In addition to the points you raise there is also the issue of re-insurance and regulation. If you can'

Yes, this one is a serious can of worms to be opening. In addition to the points you raise there is also the issue of re-insurance and regulation. If you can't get someone to cover your obligations if the odds come out against you then this is a non-starter, this is where re-insurers come in out in the real worlds and they aren't going to deal with a scheme this small so you will need something else to back your gambles. The insurance market is also heavily regulated because people actually depend on the services and the government sometimes ends up on the hook when these companies fail. To be completely honest, I can't see any way that this would A) be allowed to operate as a legal business, or B) not face some catastrophic failure down the line that actually hurts real people.