This challenge can pose some serious difficulty before you have perfect understanding of how the AI works and what the bots are supposed to do, but after you've played it several dozen times it's a cakewalk as long as the numerous glitches and AI randomness don't screw you over. It would take too long to explain every little important detail about how this all works and how it might not work, so if you need help with anything then just watch the video closely, try to replicate every action perfectly and hope for the best.
Kenny's bot has some delay on when him being alerted actually counts as Jason being detected and not just in this level, so you can actually complete the drowning a counselor with part 8 Jason with him and still be undetected at the end. Because of that, theoretically, you could do everything in this challenge in one go. It's just so difficult to do and unlikely to work that I happily settled for two playthroughs.