@LANTASKIShane also owned High North which folded in the latter aughts...
But as everyone else said...pretty much every "Pro" was either in MSP, TGR, PBP, or Level 1's movies. There were maybe 100 "Pros" between 2001-2006, which meant money was more consolidated.
My guess is that this post and the one above it are pretty accurate. There are FAR more guys now. But remember, those guys in 2000 were not for the most part making THAT much money. Gordy Pfeiffer was one of the top guys, skiing big mountain for both MSP and TGR, and he was making around 60k or something like that. Most of the guys back then were not making all that much, same as now.
There is another factor when you mention buying houses. The housing market has exploded since then, so a guy who was making 80k a year in 2000 probably could have purchased a condo in Tahoe. Now that is probably not the case.
I do think that, particularly in the park setting, the proliferation of social media has led to more athletes, and dividing revenue among more different guys. Also, guys specialize more now. Around 1999 you had Shane McConkey and Kent Kreitler in the xgames as well as filming big mountain parts. Tanner hall was doing that around 2007. Now the park events are so specialized that not only are few guys in the xgames filming big mountain, they are also only competing in either slopestyle OR pipe, not both.
I think there are probably more guys making a lot now though. It just does not seem that way because there are SO many guys who are sponsored. Over saturation of the market has occurred compared to how things were then.
Henrik Windstedt makes a lot. Or at least he used to. He made enough that he moved to Monte Carlo for his permanent residence for tax purposes. I assume you mean Harlaut though, I don't know how much he makes.