First of all, thank you for your comment. I didn't realize that linking directly to the blog post and adding the tl;dr as a comment would have been a better format. I'll remember that for the future. I do believe the tl;dr is necessary because I didn't want anyone to feel they'd wasted their time reading my entire post without having a preview.
1) You're very right. PG has likely seen more diversity than I have. However, I think his bias, when discussing the real world environment in the essay, leans toward culture that values the properties most nerds have. My bias probably leans the opposite way. So neither of us even considered a large enough environment sample as we generalized "Nerds" and "Jocks." Or perhaps PG did consider it, and that is why he alluded to the sense of greater freedom in real life.
2) This is an important idea in the essence of my post (perhaps inaccurately conveyed). Even though I considered myself a nerd, my status in high school was primarily "Jock." After high school, I was primarily a "Nerd." For me, deviating from the standard path to popularity was so much easier as a jock in high school, than as a nerd in real life. As for success after high school, I do believe nerds have a better probability overall, but anyone who disobeys the status quo in real life should expect plenty of headwinds.
3) I agree with you. My experience within a small sample of what the world offers in its entirety likely constricts my perception of the relative freedom between secondary school and real life. I only know what it's like struggling in the real world in a small farm town in MT, in a medium college-town with a population of a few hundred thousand, in Los Angeles, and in a large city in Brazil. I know what it's like to be financially successful only in that medium-sized town and in Brazil. I do believe that the lower you find yourself on the hierarchical ladder, the more imprisoned you will feel in both high school and real life.
Thank you for your insight and for both taking the time to read my blog and respond to it.