Pay it forward is a nice motto, and so is keep it playful, but I have different opinions on this than you guys probably do. The whole "Keep it playful" thing started up just before Metamoris, and I believe it was an escape hatch for the Gracie ego if a Gracie lost. I could be wrong but that is my gut feeling on it.
Pay it forward is good for senior students and lower students, etc, but I personally am a traditional martial artist, and it is in my DNA to step down before my instructor. I have always regarded my instructors with an air of nobility.
(Unless they prove that they are undeserving over time, which has happened at one club in particular)
If I was in the same division, and in a position like that, and my instructor instructed me to roll him, I would, only because he demanded it from me.
If he did not literally instruct me to roll him, I would silently back off and concede. I don't know. I just get where he is coming from.