Arrive at Hawayy Island
Get shorts from Balloon Salesman (between Shirt and Ice Cream shops)
Change into shorts in changing stations next to announcer tower
Talk to announcer and surfers to start contest
You can retry as much as you can, 10,000 points completes the to-do list objective. Build up speed by doing tricks and get the height I achieve in the video link below. The height still took me around 20 retries to finally get and its probably better to do more than just the two tricks over and over to get that height but this is how I did it.
Nailing your drop ins is also a must
Updated clip to be playable without leaving page