Your last point about flinching from hypotheses because they're undesirable is key.  That flinch is the enemy of equanimity, the acid that dissolves you to make room for Moloch.

In my head this breaks down like:

1. Split: generate alternative hypotheses.  "I believe X.  What not-X might I come to believe, and why?"
2. Commit: flesh out those hypotheses with contingent commitments for action.  This is how you know you actually generated a real hypothesis rather than just "maybe the house elves did it, wow, this rationalist stuff is easy."
3. Practice.  It might be a great rationality workout to take very low-probability hypotheses seriously and build an action plan.  "If I come to believe house elves did it, I will submit myself for psychological evaluation.  If I pass that evaluation, I will dedicate my life to documenting their existence."

Any xp with Amethyst for compare/contrast?  I'll be switching laptops soon and the biggest thing keeping me on linux is my very custom multi screen sway setup

It's one thing when you make that choice for yourself.  This is about a disagreement so heinous that you can't countenance others living according to a different belief than your own.  I read JMH as arguing for a humility that sometimes looks like deferring to the social norm, so that you don't risk forcing your own (possibly wrong) view on others.  I suspect they'd still want to live their life according to their best (flawed) judgment... just with an ever-present awareness that they are almost certainly wrong about some of it, and possibly wrong in monstrous ways.

0 or 1.  I saw this post and thought "finally!  I've been a fan since the early 90's.  I'm most surprised that it took you this long, and excited that you finally got around to it.  :)

The ratsphere is ripe for some of the same treatment you gave the fossphere back in the day.  (It's under attack by forces of darkness; it's adherents tend to be timid and poorly funded while its attackers are loud, charismatic, and throw a lot of money around; it revolves around a few centers of gravity ("projects") that are fundamental building blocks of the future - the Big Problems; etc.)

I haven't thought this through a ton, but if I squint a bit I can see Jaynes &etc filling the role of, like, Knuth and K&R and etc - hard engineering; and The Sequences/LW/SSC filling the role of, say, GNU and Lions and etc - a way for the masses to participate and contribute and absorb knowlege and gel into a tribe and a movement.  I paint that vague hand-wavy picture for you, hoping you'll understand when I say that this post feels like it should be expanded and become TAOUP but for the ratsphere.

I'm fascinated by this phenomenon, where expunging even obviously poor chunks can feel like an amputation. If you don't mind, I have a couple of questions. Have you looked at using version control for your writing? What tools do you use (Apple Notes?) and why?