Hmm, I'm not sure what to recommend as a lot of it comes from squaring my background in science with lived experience and philosophical concepts that are often kind of inaccessible, and also because I'm coming at it from multiple angles.

In my first point I mention Wittgenstein, but reading him directly is difficult to parse. "All models are wrong" is a common aphorism in statistics but I don't know if anyone's really expanded on it into a book. How to Lie with Statistics is a famous book that's somewhat related. Terry Prachett was a fan of the "lie-to-children" idea and discussed it in The Science of Discworld, which is more accessible but less formal.

My second point draws from experience dealing with people. Sometimes people are bad at expressing things or downplay their understanding, but they still have a point you can learn from. But it's also known in a philosophical context as "The Principle of Charity," or what's sometimes called "Steelmanning," as the opposite of "Strawmanning." That is, taking the strongest interpretation of someone's argument, even to the point of looking past minor discrepancies if they're not relevant to the central point. On the other hand, there's sophistry, where because of rhetorical skill, you can make an unreasonable position appear reasonable. As a thought experiment, consider that you're trying to convince a child that the earth is flat - while your position is completely wrong, you can probably "win" the argument, especially if you know more about relevant fields of science. Ancient Greek philosophers talked a lot about that sort of thing, for example Plato's Gorgias.

My third point relates to criticism of rote memorization which is often considered in the study of education and how people learn things, but I don't really have anything specific to recommend. I believe it also relates to what Deleuze was on about but I couldn't really recommend Deleuze because he's pretty inaccessible and tbh I'm not confident I actually understand him correctly.

As for my fourth point, I can recommend Zen Mind, Beginner's Mind as an introduction to Zen Buddhism. It's from a branch of Zen (Soto) that de-emphasizes koans, but Buddhist teachings in general are often written in a way that is contradictory on the surface level. If you want something that's more modern and Western in style, there's Hardcore Zen, though it's not for everyone, if the Pig Poop Balls analogy I used resonates with you you'll probably get something out of it. Generally I wouldn't recommend trying to approach koans before understanding a bit about the broader theory and practice of Buddhism.

Sorry that that's completely all over the place but like I said I'm using multiple angles here and they come from many years of personal experience butting my head against a wall and trying to be super logical all the time and dismissing perspectives that didn't fit within that framework before finally arriving at various realizations that critiqued that approach.