Hello Buildingblox.
Thank you for giving the game a try, and giving such descriptive feedback.
My idea for the first race is, that you should come around 4-6th place if entering it at once which should give some sort small reward. Then to win the race you would have to spent a couple of skill points in one of the categories. If choosing climber, the win condition should be the first hill. If springer, it should be the finale, if soloist it should be breaking away in the tailwind after the hill.
I'll work with the scaling to make sure this desired outcome is hit :)