As to that jump master, he has already made many, many jumps himself and knows whereof he speaks.
But he is still landing with the plane. And I have personally seen a Jumpmaster accidentally hit the black button and deploy his chute inside the aircraft so it does happen that “risk” rears it’s ugly head from time to time. I knew a guy who had 500 jumps, Special Forces and crashed and burned at an air show in Hawaii. He lived through it but it took a year to walk again.
Risk/Benefit can be a very complicated thing.