I’ll preface my comment by acknowledging that I’m not a regular LessWrong user and only marginally a member of the larger community (I followed your link here from Facebook). So, depending on your intended audience for this, my comments could be distinctively useful or unusually irrelevant.
I’m terribly grateful for the context and nuance you offer here. The guidelines seem self-evidently sensible but what makes them work is the clarity about when it is and isn’t worth tolerating extra energy and pain to follow them. A few notes that are almost entirely meta:
1) I suspect that nearly all objections people have to these can be forestalled by continued editing to bake in where and how they properly apply—in particular, I imagine people emotionally reacting against these because it’s so uncomfortable to imagine being hit with criticism for not following these guidelines in cases like:
A public opinion or social conflict situation that is definitely not a collaborative search for truth
Sharing painful emotions or calling attention to an observable problem
Seeking help expressing a nascent idea or self-insight that has to go through a shitty first draft before one is ready to communicate it with nuance and precision.
Your expansions make it perfectly clear that you recognize situations like these and believe people should handle them in effective and/or compassionate ways—my impression is that they either don’t fall into the domain of “rationalist discourse” or that rationalist discourse can create a container allowing not-rationalist-discourse to exist within it (as you described in the comment thread with LoganStrohl about signaling when something is poetry). So I’m mentioning them only to call attention to misreadings that might, with superb editing, be avoided without weighing down the language too much.
2) I’d be interested to know more about how you see this resource being used. If you see it as something that could become a key orientation link for less-experienced members, then perhaps including a little bit of expansion amid the list would be helpful. If you see it as something that experienced members can point one another to when trying to refine their discourse, it might be useful to promote a little bit of the text about not weaponizing the list / not using it as a suicide pact into the main text.
3) I also think the “43 minute read” text runs the risk of turning people away before they’ve even read the part about how they don’t have to read all of it; once you have a stable draft you could consider creating a canonical link with just the short version and a link to the full expansions. (even people who are willing to put in the effort to read a longer piece might suffer because they think they need to save it for later, instead of reading it immediately at a time when it would be helpful to a conversation).
4) Finally, I think some of the comments might reveal some confusion among readers about what parts of this are intended as universal norms for good communication vs. universal norms for clear thinking vs. a style guide for this particular website (your expansinon regarding how guideline 1 applies to idiomatic hyperbole suggests that it’s at least a little bit of the latter). If this is to be an enduring, linkable resource then it might be helped by more context on that point as well.
I’ve heard some people describe the unnaturalness of the pomodoro method as a benefit. The reasoning is that if you take breaks when you feel like it, you’re likely to do it 1) after completing a task and before starting the next one, or 2) when the task you’re on becomes unusually unpleasant. This timing makes it more difficult / painful to get moving again after the break. If you instead take breaks when you’re interrupted by a timer, there’s an obvious point at which to resume and a flow to get back into. You might even want to get back to what you were doing. I’ve found this somewhat true for myself.
The downside to this approach is that you’re more likely to lose a lot of state than if you take breaks at times that feel natural. I don’t know if there’s a good way to combine the two.