If people want to try more dangerous stuff, there’s a holodeck with safety for that. So there isn’t much reason to risk more pain and injury than necessary.
Like now, medical care is still just a backup if the normal means of self-preservation fail. You can never be sure if that stunt will end up with a broken leg or neck, and there’s a thin line between those, even for ST-level docs.
But then there are species that will always push to the brink of survivability, like Klingons or Hirogen.
Ed: but specifically for mild things like skating, that’s more about having your past injuries healed so they don’t “remind” you to not do it again. But again with a hoodeck that’s less of a problem.