I read only the "landmark 1961 essay, Introduction to the Study of Practical Wisdom". The book is pretty hard to find.
I felt disappointed and relieved at the same time with Simon's conclusion. It is intellectually humble, which is great, but also an appeal to faith in the final analysis - in Simon's case, faith in a rational social order.
I liked his discussion of deliberation, and his striking distinction between theoretical and practical wisdom.
I liked his mountain climber story.
I found the application of the scholastic apparatus to the subject obscure and tedious.
Superb, and a mixed bag. I will re-read it a third time later.