Hacker,
I would gladly pay $25 for a professional ebook rendition of the
Harvard Classics 5 shelves of books. It's available
online from Bartleby in HTML form.
It's probably the most classic, well-conceived and respected collection of reading available. In fact, reading them was compared to having a full college liberal arts education. I probabaly got that a little wrong, but something like that.
Even better would be if book by book detailed commentaries could be integrated, but I'm afraid something like that is likely to be beyond even your capabilities.
No, I don't have a source for such commentaries or even know how to find them. I would be thrilled if someone can point me to a place where they exist.
Bob