I think you hit upon something. I didn't see that first season, alas. However, even I thought this challenge wasn't as funny as the previews tried to make it look. Thinking back, I remember once when I went innnertubing down a snowy hill with a group of friends. Half the fun was standing at the top, waiting your turn, and laughing your rear end off whenever somebody fell off. When you in turn fell off, it wasn't nearly as embarrassing because you could laugh with the others.
So, yeah, this challenge fell flat. Now, if you want a real challenge with cheese, send the racers to Gloucester, England for the annual Cooper's Hill Cheese-Rolling Race. As the name implies, racers must send a huge wheel of cheese rolling down a steep hill, then go chasing after it. The first person (not cheese!) to cross the line at the bottom wins. The winner is then expected to get his/her cheese back to the top of the hill, preferably shirtless if you're a man.
I think I would love to see the Hockey Brothers participate. It might get a little scary with the YouTubers, though.