Correct, my chances would hinge on the stick resurfacing and making it to 42 shaves. Suddenly I feel like a Jacobite: long live the king across the water!
Ah, but I think I see the joke now. If the final count is 34, Bob wins. If it's 37, Bob wins. So either count is quite fair. You could hedge against the 1-2 shaves possibility by declaring a tie between Bob and Nathan, but I think the probabilities are with Bob.
And the prize? Does he win the post of trail boss for the next round?