I'm thinking of going a different route. Imagine a GitHub repo consisting of book titles together with an interesting selection of problems, decided upon by the user group. If the initial repo focused on statistics, and built on a sequence from introductory probability to descriptive and inferential statistics to regression and generalized linear models and on to stochastic processes and Markov chains, this could serve a segment of the interested population. Several books could be detailed with a recommended order both of books and of chapters. The problem selection could be contributed to and decided upon by users via pull requests and the like. Maybe it includes hints for some of the harder problems, or links to relevant documentation.
This achieves an experiential parity for users. You and I, who happen to be working on the same section of the same book, can work together as we choose. A common set of materials helps us help each other and ourselves. It also stands as a resource for many of the questions found on some forums regarding self-study plans and book recommendations. Book recommendations help, but having a body of other students available to mentor or share approaches improves upon that.
With this framework defined, the project could be forked for a different goal or curriculum. If someone wanted to include some of the texts but rather than progressing through statistics wanted to build out a plan for studying statistical mechanics or differential equations, that's easy enough. No work is wasted or duplicated.
I'm going to start fleshing some of this out for my own planning but if this strikes anyone's interest we could discuss how to make something like this work. The motivation is selfish: for any topic I can find five eagerly recommended books but developing a way of choosing and using the book, and a larger plan for progressing beyond the book, isn't so straightforward. By definition I don't know what I'm doing.
Maybe something like this already exists. I know there are the likes of Coursera, Udacity, etc., and I will be looking at them some more. I haven't found very much beyond the basic undergraduate work, however. This potentially allows for any arbitrary book, of any sophistication, to be made a shared learning experience in an ad hoc fashion.