I like your solution to pascals mugging but as some people mentioned it breaks down with superexponential numbers. This is caused by the extreme difficulty to do meaningful calculations once such a number is present (similar to infinity or a division by zero).

I propose the following modification:

• Given a Problem that contains huge payoffs or penalties, try common_laws solution.
• Should any number above Gogol be in the calculation, refuse to calculate!
• Try to reformulate the problem in a way that doesn't contain such a big number.
• Should this fail, do nothing.

I would go so far as to treat any claim with such numbers in it as fictional.

Another LW classic containing such numbers is the Dust Speck vs. Torture paradox. I think that just trying to calculate in the presence of such numbers is a fallacy. Has someone formulated a Number-Too-Big-Fallacy already?