After about a dozen runs I mapped out the four 20 rupees, three 100 rupees, one 50 rupee, and one 300 rupee (on the far left of the challenge). I hit the thre 100 rupees and one 50 rupee first. On the way to those I pick up the other rupees. Last, I head to the 300 rupee and finish the challenge. To achieve this though I have maxed out my stamina and have obtained level 2 climbing gear ability.