Great question.
My joke answer is: probably Hegel but I don't know for sure because he's too difficult for me to understand.
My serious answer is Graham Priest, a philosopher and logician who has written extensively on paradoxes, non-classical logics, metaphysics, and theories of intensionality. His books are extremely technically demanding, but he is an excellent writer. To the extent that I've managed to understand what he is saying it has improved my thinking a lot. He is one of those thinkers who is simultaneously extremely big picture and also being super rigorous in the details and argumentation.
Ever since I first studied formal logic in my first year of undergrad, I always felt it had promise for clarifying our thinking. Unfortunately, in the next decade of my academic education in philosophy I was disappointed on the logic front. Logic seemed either irrelevant the questions I was concerned with or, when it was used, it seemed to flatten and oversimplify the important nuances. Discovering Priest's books (a decade after I'd left academic philosophy) fulfilled my youthful dreams of logic as a tool for supercharging philosophy. Priest uses the formalisms of logic like an artist to paint wonderous and sometimes alien philosophical landscapes.
Books by Priest in suggested reading order:
An Introduction to Non-Classical Logic: From If to Is. Cambridge University Press, Second Edition, 2008.
Beyond the Limits of Thought. Oxford University Press, Second (extended) Edition, 2002.
One: Being an Investigation into the Unity of Reality and of its Parts, including the Singular Object which is Nothingness. Oxford University Press, 2014.
Towards Non-Being, 2nd (extended) edition. Oxford University Press, 2016.
Science and Sanity by Korzybski is a great book but quite heavy. It's where "The map is not the territory" comes from.
The Emprint Method by Leslie Cameron-Bandler is a great work about how to model mental processes but also very dense.
Science and Sanity looks pretty interesting. In the book summary it says he stressed that strict logical identity doesn't hold in reality. Can you say more about how he builds up a logical system without using the law of identity? How does equational reasoning work for example?
It seems like the internet in general, and social media broadly, e.g. LessWrong, has this problem that there's a lot of data. The data has to be filtered somehow. The main way data is filtered is by (1) recency, (2) backlinks, and (3) upvotes.
One problem is that these filters don't distinguish between stuff that's not upvoted or backlinked because it's not so good / interesting / important / novel / true / useful / etc., vs. stuff that's not upvoted or backlinked because it was hard to understand (or, easy to misunderstand as not good) and therefore didn't meet the threshold for being signal boosted. In other words, we aggregate signals of "I don't know about this yet" roughly the same way we aggregate signals of "This isn't good enough that it should be remembered much".
This seems like potentially a big problem, or rather, a big opportunity. Maybe there's good ideas that didn't spread much that we could revive. Maybe ideas would develop faster if people could expect that other people would remember "there's an open question here" rather than just not remembering. But IDK how big of an opportunity it is, so I wonder:
What are some examples of works (of any kind whatsoever) that were / are hard to understand, and so didn't get signal boosted when they were new enough to have attention directed to them to become understood, but instead got lost in the shuffle?
One of the famous examples around here is [Infrabayesianism](https://www.alignmentforum.org/posts/83DimRqppcaoyYAsy/job-offering-help-communicate-infrabayesianism). Maybe some of [Donald Hobson's work](https://www.lesswrong.com/users/donald-hobson) gives examples. What else?