'Why are we teaching a generation of students to use crippled technology?'"
Because we don't really want them using advanced technology on the exam in the first place. We want them to know the theory. Graphing calculators have limited uses (in my university, it is almost never actually useful) so they still require some thought before using them to solve a question.
Advanced technology is advanced enough to solve problems without the student needing to know the theory in the first place, and advanced enough for teachers to not know how to shut off that functionality. That's all.
Committed members like this, that sacrifice their time and effort, are what keep the open source movement alive and churning out functional code. So in the end, he left the world with a legacy of improving software for everyone else, doing what he loved, and cleaning up loose ends. Can't blame him at all.
The quote "explore controversial topics without fear of reprisal" sounds like the kindle for a flame war to me. It just means that teachers can make fun of or downplay topics that other teachers are teaching "without fear of reprisal".