My problem is part style, and part content. Stratechery reads like it's written to be narrated - rather than exist first as writing. There's verbosity, pauses, long sentences, etc. And then you listen to the narration it makes sense.
But that complexity makes reading harder. Not saying everything needs to be 5th-grade-level, but complexity isn't required. Paste a Stratechery article into Hemingway Editor to visualize my point.
The stats below:
Readibility - Post-Graduate (aim for 9)
26 of 44 sentences very hard to read
8 of 88 sentences hard to read
31 weakeners
6 words with simpler alternatives
What a chore to cover, and that's without commenting on the ideas/concepts in the content.
I'm sure some folks like this writing style but I don't. And try hard to write my newsletter and other prose with far less complexity.