I spoke with Charlie this past week and we both decided that my first idea is my best one. So, I decided this was the one I was going to pursue my penetration testing idea and found 6 more articles for this.
A couple of the articles I found were about professors having/teaching a first-time hacking course. It was really cool to see the different designs of the classes. There was a general theme of keeping a subset of computers in a controlled environment and then allowing the students to work from there. One article included a complete description of their syllabus and the assignments of the course. This was helpful as it gave me an idea as to what software was being used in these courses.