I'd suggest that both you and he read The Teenage Liberation Handbook. It is the book for teen's unschooling and you will be pleasantly pleased by the high bar the author sets for what education is, but all the work and drive is the student's.
I like Christopher's bio of his dad, and in college I had to write a psycho biography of somebody. I did Tolkein and used Jung as my psychologist. I used this book: http://www.amazon.com/The-Individuated-Hobbit-Archetypes-Middle-Earth/dp/039528208X/ref=sr_1_1?ie=UTF8&qid=1370006632&sr=8-1&keywords=the+individuated+hobbit