The problem is that your top-tier book for one person isn't a top-tier book for another, and then there's different kinds of top-tier books, ones that focus on depth vs ones that focus on context. I think it should be possible though to identify these books, classify them based on depth vs breadth vs context, and then put them in sub-tiers (eg layman, motivated amateur, budding specialist, master).

Getting back to the individual though, it's very hard to know how big of an inference gap there is for the model(s) you're trying to convey and how much the person "knows" already. Some books are masterful if you've read precursor books a, b, f, and p. Some books are masterful if you're coming from the right cultural context. And then there's tightly held biases that can get in the way of some core assumption of the book, ruining the whole effort.