You're basically describing The Skateboarder in the High Castle. Steve Rocco remains a used car salesman. Rodney Mullen, a former pro freestyle skater, is a nameless, faceless scientist working for Space X. He has high blood pressure due to stress, but his teeth are all present and in excellent shape thanks to the dental plan. The X-games dropped skateboarding's half-pipe event for aggressive inline. Thad Henderson's Pro Blader is basically the same as THPS, but the soundtrack contained only nu-metal, 90's punk, and "techno." Hip Hop never grew past late 90's mainstream before fading into obscurity. Sugar Ray, however, made the transition through the 00's and continues to sell out arenas to this day. The rise of electronic music, incidentally, occurred without incident. Snowboarding is somehow shittier. Trousers never became tighter in the 2000s; rather, they became much, much baggier until a global denim shortage forced leading manufacturers to begin making reasonable clothing once again. Monster and Red Bull never became the corporate dynamos we know today, instead Tab Cola reigns supreme. Roller derby now takes place on skateboards, but everything else about it is pretty much the same.
In 2018, small fledgling groups of skateboarders would begin reappearing in parking lots and skate parks around the world, though it is estimated their population will never again grow greater than that of their natural predator, the wingsuit kid.