Clever readers may be saying to themselves: "okay, but doesn't all this also make the chances of encountering black swans higher as well?" We will address these concerns when we talk about principles three and four.

Did you address this later, or is that coming in part 2? Also, I'm not sure if I understand this concern. If I were just exposing myself to more variance, then yeah, I should be worried about increased bad luck as well as good, but maximizing options doesn't seem like the same thing as increasing variance. Though maybe that's what you were going to say. :)

Btw, the focus on option maximization, especially in the ESR quote, reminds me of Alex Wissner-Gross's Entropica, which you might also find interesting.