It’s probably a bit late now, but I thought I would share my experience with How Should We Then Live. I had to read it in a college world history class, and I really struggled with it. I got about 2/3 of the way through, and he finally got to his point! (The way an artist does his art is influenced by his world view, therefore we can learn a lot about how people or historical groups thought by analyzing their art.) As soon as I saw that, I thought, “OH, that’s what I’ve been supposed to get all along!” Then I wished I had time to read back through the book and see what I had missed, but of course, as a college student, I did not have the time to do that!
So my suggestion would be to help the student understand where the book is going before he starts it, so he can see what’s going on along the way. Perhaps that’s only important for a global-to-parts learner, but I could not piece it together from the detailed parts Schaeffer was presenting, at all. It would have helped me massively.