EXTREME SKIERS WHO COME TO JACKSON HOLE inevitably face one of three choices: (1) Move back east, go to work for the Man, and ski twice a year. (2) Continue to suffer a dozen roommates or live in your van down by the Snake River. (3) Evolve fiscally by selling the Man an expensive-ass "Hummer House," and repeat as needed.

Some choose door number one. Justus Meyer, a big-mountain skier who lived in the house after graduating in 2005 from Harvard, where his father managed the university's endowment, is now working in private equity in London. Housemate Mark Longfield, 29, left Jackson in 2006 to practice business law in Delaware; four months later he was back, working remotely for his firm. Meanwhile, plenty keep eking out a living through door number two, patching together sponsorships and service jobs. But in the last several years, number three has become the ticket for an increasing number of winter athletes hoping to make it in one of the richest counties in America, where, as of July, the median home sale price was $1.175 million, 28 percent higher than in 2006.

Snowboarding mountaineer Stephen Koch got his Wyoming real estate license earlier this year. Olympic biathlete Erich Wilbrecht went from guiding fly-fishers on the Snake to hawking real estate in 1993. Next to the weather, it's what everyone in Jackson talks about. "Any ski bum who worked hard, begged, borrowed, or stole to buy real estate in ski towns before this past wave was lucky and/or smart," says Rob DesLauriers, 42, a ski mountaineer and Jackson real estate agent who allowed his friends first crack at condos in his slopeside Hotel Terra, a 32-unit green development opening this winter. "I loved living in my van and on friends' floors, but it gets tiresome," says DesLauriers, who in 2006, along with his wife, Kit, and photographer Jimmy Chin, made the first American (and, for Kit, first female) ski descent of Everest. "Then at some point we seem to change a bit, and that's natural. We want a house, the van died, etc., and then, yes, it's hard. Usually the ski celebrity doesn't choose to get older and passé. It's going to happen—so what are the options? Going from star to anything is tough."

"Real estate is a great avenue for athletes," says Rick Armstrong, 37, one of the first professional freeskiers in Jackson. "I love to see someone use their mind so they can live here." An Alaska heli-skiing pioneer and fixture of myriad ski flicks, including the upcoming December release Steep, "Sick Rick"sold his Toyota four-banger pickup and a garage full of ski gear in 1994 to make the down payment on a $110,000, 1,200-square-foot condo with his wife-to-be, Holly Menton. "It was the least expensive condo in Jackson," Armstrong says. "Two years later, after a full-on remodel, we sold it for $230,000. Now the price of entry here is crazy expensive. A bottom-of-the-barrel, 600-square-foot condo starts at 340 grand. And that's in marginal repair."

"I actually looked at Charlotte's house when it was for sale," Armstrong says. "It needed a lot of love. A lot of sweat equity."

Charlotte has drawn heavily from her line of sweat equity. A small-towner from Fairlee, Vermont, she's no trustafarian investing with Monopoly money. "My dad was a hippie," she says. "My parents didn't believe in debt—at all. Not even a simple mortgage. Cash for everything." Her father, software designer Alan Moats, raised the family's vegetables, raced on the World Cup telemark circuit, and entered Charlotte in her first race when she was seven. (She won a cookie.) At 12, she enrolled at the Burke Mountain Academy, a ski prep school in northeastern Vermont, and at 14 she was the 1995 Junior Olympic slalom gold medalist. She switched to freeskiing in 1999, ditching a racing career at Dartmouth to spend winter terms off, traveling and competing. Her athleticism, along with her looks, got the attention of sponsors like Spyder, Völkl, and, currently, Columbia Sportswear. Her reputation for nailing big, poetic lines got her segments in the Warren Miller films Storm, Impact, and Off the Grid, as well as Teton Gravity Research's High Life.

Charlotte's foray into real estate began in 2003 with a condo replete with bad shag and puke stains on the wall—the former band pad for the Mangy Moose Saloon. She scraped to save eight grand, a 5 percent down payment on the $160,000 price. Then she traded up, selling the condo for another, less urpy place in town and ditching that for the SKI House. "As the house increases in value," Charlotte says, "I borrow back against the new appraised value by either refinancing the entire mortgage or taking out a home equity line." Until last summer, she was also working part-time for Countrywide Home Loans, processing mortgages on her kitchen table.

But a window may be closing on the flipping scene, as this year's mortgage crisis attests. Locals are discovering that, like a favorite run tracked out by 9 a.m. on a powder morning, an easy loan is a thing of the past. "Now you have to have 20 percent down and a strong credit rating," says Armstrong.

Add to that the fact that there are only so many bargains in a town like this. "All of the really horrible places are getting gobbled up," Charlotte says, the corners of her mouth turning down. It's clear that this is a shame, that one day soon the vomit stains may be gone.