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Very interesting read. It looks to me like the post identifies 3 main problems with the essay medium:
1) The knowledge is dispersed and not indexed.
2) Knowledge becomes obsolete relatively quickly as new insights/better explanations are generated relatively frequently.
3) The context of communication around digital essays is not adequate for high-effort learning mode.
Modulo the motivating problem you mention, the digital textbook medium you propose seems to solve all three, assuming new, revised "editions" are released every now and then. Do you have any thoughts about how it compares with a Wiki medium?
I have recently started trying to organise my writings and I am also unhappy about the limitations of the essay medium. 3) is not an issue in this case, but I am quite bothered by 1) and 2). I also worry about:
4) The essay medium has a linear structure; expositive text generally does not.
It seems that the structure of expositive text is more similar to a tree-like graph: often there is an explanation about a particular idea X, and then the flow of the text "branches" into different topics to be discussed after introducing X (though paths sometimes rejoin). Perhaps this is not a big issue, but right now I feel like I'd prefer a medium that reflects this structure.
5) Explaining ideas in detail makes it harder to follow the big picture.
On re-readings of the material, sometimes I wish I could "compress" explanations I already understand to focus on the higher picture and relations between ideas. Skimming seems the thing to do, but it requires some sort of indexing, and right now I feel like digital media should be able to offer more powerful ways of doing this.