2) I disagree on 2 counts.
a) Thinking you'll get away with something is categorically different from knowing it. Nobody ever experiences this sort of assuredness and we cannot extrapolate our behavior under volatility to conditions of certainty. The closest we come to it are the most meaningless actions (like me reaching for a water bottle, "knowing" that I will touch it and lift it up), but no meaningfully large action, and certainly not a single one that involves other conscious beings is ever experienced as certain.
b) Humans are not fundamentally probability-modeling animals. When your bottle slips and shatters on the hiking trail, nobody - not a single human soul - runs Monte Carlo simulations on where those shards might end up and what that might mean for the future of humanity and "solves back" the right action. It is a complete category error to model human actions as such. Probability estimates have their (limited) place in (rare) human decisions, but even then it is not an exact fit.
This whole crystal-ball exercise is at best a lazy attempt by Lee, because it is easy and convenient to talk about the robo-human caricatures of his imagination. He is basically shaking his fist ADMONISHING YOU to behave more like the simplified easily-quantified caricatures so he can study you easier get his MacArthur Genius Grant goddammit.