It's a parody of time share sellers and teen sport movies. The new kid gets antagonized by the...well antagonist for no reasons other than he being the protagonist, there's a popularity loving girl who chats or even firsts with the protagonist and it's instantly determined that he stole it from the antagonist, the nerdy but actually hot (and they literally said this in the episode) girl takes the stage and it's painfully obvious that she likes you (for little to no reasons) and that you'll probably end up with her instead of the bitch (Zookeeper). The protagonist loses an humiliating defeat but the antagonist still stupidily bets something incredibly large for a rematch, again for no reason they cheat even when they could had legally won and that's their downfall, be it in the race or someone finding out later. It was all summed up pretty nicely by Stan at the end. Also in real life a few hours or days of training doesn't raise your skills by 20 levels.
The joke about the time share is that, well time share really go out of their way for sells. Also I think it's a little too much to judge this episode so much when you yourself have admitted that you didn't knew what they were parodying.
Do yourself a favor and watch Better Off Dead, an '80s ski comedy that was among the films parodied in this episode. You could also watch another Cusack film, One Crazy Summer, which lacks skiing but does contain the element of the Teen Center being shut down unless our hero wins some ridiculous contest.
(This has long been one of my favorite South Park episodes.)
Oh, and the weird breasts are a reference to the (original) Total Recall movie.
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Asspen
I have seen all but 3 episodes of season 6 and I can safely say that I enjoyed all of them, other than this episode. I don't know what this episode was supposed to parody, or even if it did parody anything, but it wasn't funny. Stan, Kyle, Cartman, and Butters go on a ski trip and meet this dick who targets Stan for no reason and is dating somebody who he thinks is Stan's ex-girlfriend, even though he never met her. He challenges Stan to a ski race, and beats him. And there's this community center that's about to be taken down, so Stan rematches the guy, wins, saves the center, get's his not girlfriend back, yada yada. The point is why? What was the episodes point? I never smiled when I watched this episode. It seems like it's just a bunch of older people focusing on Stan because he exists. The whole main plot is just one joke. Stan and some of his friends lampshading that he doesn't know these people, and it got boring fast.
The sub-plot is also lame, but not nearly as bad. There's these two insurance guys for time share who repeatedly get the parents into meeting into buying a condo. They try to leave reoeatedly, but always fail. And then when they call the police, it turns out they're working for time share also, and threaten Randy and the other parents with guns. Next scene they appear in, they're perfectly fine. They bought the condo out of force, but my problem with the sub-plot is that it feels rushed all together, and the only real comedic aspect is the parents getting annoyed. Also, what is up with one of the community center people and her mutant breasts? What's that supposed to mean?
My recommendation, don't watch this episode. See the other episodes of season 6. They were hilarious. This was not. It's probably funnier if you know what they're supposed to be parodying, and maybe if I saw the thing they parodied I would like this episode, but since I didn't, nor did they even bother to add jokes outside of it, it feels more like a bunch of idiots focusing on Stan for no reason. This is an episode that's about as lame to me as the season 1 and 2 episodes. Rushed, unfunny, and overall, boring. 2.5/10
Note: I probably didn't explain the plot enough, but I don't know how to put it in any other word, and with the word limit on tv tropes, I'm pretty limited.