Whereas you cannot go wrong with any Frank Ching book as already suggested ( I’d go for ‘form space and order’ ) , if you are looking for a super light read ( and perhaps a little tongue in cheek humour ) may I recommend to you 101 things I learned in architecture school.
This book is great, even though it probably won't answer any of the questions you have.
/r/architecture/ Has a ton of Arch students and grads, I would post your question there and see the myriad of responses :)
Do you know if he'll actually be drafting by hand? A lot of schools are all digital now.
As an alternative, here's a set of items I would have loved to receive as a freshman in architecture school:
and a nice sketchbook. I'm a fan of the dot grid ones. The Frank Ching books are invaluable. I wish I still had my entire collection.
If you have a short attention span and like lists: 101 Things I Learned in Architecture School
I like this one too
http://www.amazon.ca/101-Things-Learned-Architecture-School/dp/0262062666
EDIT: Well I enjoyed it...