[maxdemarzi]

I apologize if this post comes out sounding very negative, but "Insurance" is susceptible to negative Black Swans.

http://specialtyinsurance.typepad.com/specialty_insurance_bl...

Any algorithm you come up with will eventually meet a large sigma event and destroy your system unless it includes a whole lot of exclusions, or inversely unless it covers only very specific events.

Tackling Health seems daunting to me, maybe start with some kind of property insurance (computer insurance against theft/damage?)