This is a throwaway account. I'm a pretty regular poster here and don't want to seem like a name dropping douche bag. I also don't want to doxx myself or the person I'm talking about so I am being intentionally vague.
I grew up with, am very good friends with, and regularly ski with someone I would describe as a "mid-tier" pro skier. He has competed on the FWT, and has had a titled segment in the last four movies from a top two ski movie company (and filmed again this year for another segment next year). He has been on the cover of Powder, Skiing, and a bunch of other magazines. I often see him in banner ads on ski websites. He has several major sponsors and thousands of social media followers, I have seen clips of him posted here at /r/skiing several times (I was even in one of them for about 5 seconds, AMA), etc etc. Just trying to establish the level of "pro" that we are talking about.
He doesn't really get regular pay checks from his sponsors. We don't really talk about his money situation much but he lives in an average apartment with two roommates and bartends at night. His sponsors give him money for traveling and he gets kick backs when he gets their product in a movie, magazine, etc. I would be very surprised if he could not qualify for the contest mentioned in the OP.
On the other hand, everything free if it is related to skiing. Everything. All gear, travel, lodging, etc is paid for if it is related to skiing. He spends most of the winter storm chasing or filming. When he's home he's working nights and skis every day.
He's a local born/raised in our (very prominent/famous) ski town and people gravitate to him like none other. Rich people offer to take him on trips just so they can say he was with them. I mentioned he is a bartender... he could get a job in any bar in this town at the drop of a hat because he brings in so much business. People love being served by the guy on the blow up magazine cover hanging on the wall. And of course the fairer sex eats it up.
It's a pretty awesome life. Don't be sad.