Yeah, as much as Moldbug likes to talk about his site as a "red pill" it's really a horrible place to introduce yourself to Neoreaction. He is stingy with citations, assumes a lot of prior knowledge, and seems to assume his readers are either archive-binging or regulars.
the bit about Order, Chaos, and Cathedral are all so layered in metaphor that I'm not really sure what they actually mean
The Cathedral is a less clunky and more memorable way of saying "the bureaucracy of the international Progressive (he prefers Unitarian or Communist, but the territory is the same) movement and aligned criminal organizations." It's not exactly your standard conspiracy theory as there are no leaders, no actual plot, not even a conspiracy per se; just people reacting to a really bad set of incentives which drives politics leftwards and increases governmental entropy. It's an ideological feedback loop; a memetic parasite which gets more powerful by creating conditions hostile to its host.
Order / Chaos is really just a D&D-laden way of articulating Hierarchy v Anarchy. An Ordered society has clear lines of authority stretching downwards from the top (Moldbugian Formalism literally means making sure Formal de-jure authority and informal de-facto authority line up), with an incentive structure which promotes civilized behavior through appeals to morality and self-interest. A Chaotic society has unclear and/or conflicting sources of authority, such as imperium in imperio, and the incentive structure promotes societal conflict.
In terms of evidence, he alludes to some but you really need to come in with your own knowledge for the most part. Learn more about the biology (genetics and epigenetics) of intelligence, as well as other physiological differences linked to race / sex, a little macroeconomics and some history and you'll be able to make most of his points better than he can. Just ignore the climate skepticism and Chicago School stuff, put it down to him not having a science background. His crime stats are interesting but highly contested; his stats show a roughly 35x increase in reported murder over the last two centuries (that's after the recent crime dip; it was 50x in the mid 20th century) but people have claimed that it can at least partially be explained by poor record keeping.
Personally, I suggest you read him as a sort of autocthonian Free Spirit; someone who independently came to realize the need for a transvaluation of values and to avoid becoming a civilization of Last Men, but without either the elegance or nascent transhumanism of Nietzsche himself.
TL;DR: Moldbug is not user-friendly. If you want to get the most out of him, use your own prior knowledge and steelman his philosophy then have it fight with yours. The results may surprise you.
just people reacting to a really bad set of incentives which drives politics leftwards and increases governmental entropy
Drives politics leftwards: This is confusing to me because I'm sitting leftward. This insidious set of incentives is shifting society's values towards mine. I want this to happen. Am I supposed to be rubbing my hands together and cackling gleefully as Cthulhu does my bidding?
Governmental entropy: So, the way you phrased that makes me assume that this doesn't mean "overturning of social order via revolution". But what does t...
People want to tell everything instead of telling the best 15 words. They want to learn everything instead of the best 15 words. In this thread, instead post the best 15-words from a book you've read recently (or anything else). It has to stand on its own. It's not a summary, the whole value needs to be contained in those words.
I'll start in the comments below.
(Voted by the Schelling study group as the best exercise of the meeting.)