
I think perhaps the best bang for your buck could be Wheeler's Understanding Variation -- but that is based mainly on vague memory and skimming the table of contents. I plan on writing a proper review of that book in the coming year to make certain it is what I remember it to be.
I think the earlier works by Taleb also touch on this (Fooled by Randomness seems to have it in the title).
But then I strongly recommend branching out to places where these fundamentals are used, to cement them:
- Anything popular by Deming (e.g. The New Economics)
- Anything less popular by Deming (e.g. Some Theory of Sampling)
- Moneyball
- Theory of Probability (de Finetti)
- Causality (Pearl)
- Applied Survival Analysis
- Analysis of Extremal Events
- Regression Modeling with Actuarial and Financial Applications
The more theoretical and applied books are less casual reads, obviously. They also happen to be the directions in which I have gone -- you may have more luck picking your own direction for where to apply and practice your intuition.
Edit: Oh and while I don't have a specific book recommendation because none of the ones I read I have good opinions on, something on combinatorics helps with getting a grasp on the general smell of entropy and simpler problems like Monty Hall.
I recently re-read and took extensive notes on de Finetti's Theory of Probability which I always recommend. But don't stick to just that.
I recommend you start with these basic theoretical books to get a sense of what it's all built on. But then if you want more practical advice about how to handle things, books on sampling theory tend to hit a sweetspot between theory and practise, in my experience. I like Sampling Techniques (Cochran, 1953) and Sampling of Populations (Levy & Lemeshow, 2013).
These things have helped me understand probability and statistics a lot better. Some examples of books that have been useful include,
- Understanding Uncertainty (Lindley 2009),
- Theory of Probability (de Finetti 1975),
- Foundations of Statistics (Savage 1953),
- Computer Age Statistical Inference (Efron),
- Causality (Pearl 2011),
- Trustworthy Online Controlled Experiments (Kohavi et al.)
However, most of this is about one "person" dealing with "the world", which in turn is neutral. I want to learn more about the situation where two "people" are in an antagonistic/competitive relationship.
I mention these to give an idea of what sort of book I'd prefer: I want to go into technical detail, but I don't need everything to be proved from axioms. I will eventually use the tools I learn in practise, but I do want an intuitive sense of what they mean and how they are constructed, and I'm prepared to work a little bit for it.
If I can't get a better suggestion here, von Neumann's classic on the subject is where I'll go.
https://onlinelibrary.wiley.com/doi/book/10.1002/97811192863...
Jaynes is certainly very deep and some sections are harder than others. It's interesting regardless of your level (this is a book worth rereading several times).
For a less technical, but full of insight, introduction see Dennis Lindley's Understanding Uncertainty:
https://onlinelibrary.wiley.com/doi/book/10.1002/97811186501...