One measure of this type of writing is whether the ideas pattern match situations by association before you've fully digested them. I fear he'll hate this entire idea for failing to understand mediocrity (which I don't) but @vgr was probably the first person whose writing did this for me.
Another angle on this is that I'm relatively more excited about writing and coding assistants that improve quality than I am about tools that help me write more prose or code.
You're talking about density I think, which is orthogonal to mediocrity. I wrote about it in a couple of posts ~2012. You're on to something. Density comes from tighening grounding https://www.ribbonfarm.com/2012/01/11/seeking-density-in-the-gonzo-theater/ https://www.ribbonfarm.com/2012/05/03/rediscovering-literacy/