I wonder if it would be possible to build a wagering/probabilistic Zendo crossbreed. That is, the computer is willing to be Dutch-booked, if you can only correctly estimate the probabilities given some examples. You might even be able to make scenarios representing various failures of rationality, like the Linda example ("green is more likely than red; stars than triangles; smiling than frowning; bouncing than glowing -- now, which is more likely: the star, or the green, bouncing, smiling star?", or the 2-4-6 case, or maybe even the Availability heuristic (the system will be inclined to show you examples where you made a lot of money, in contexts where betting on them would lose you money).