Of all skateboarding sponsors, if anyone provides health insurance it's probably not the board companies. If any do, it's probably the drink companies like red bull and mountain dew, or the shoe companies like nike and DC. I just don't see a board company like Foundation or Toy Machine having the ability to offer health insurance to its riders. Maybe some of the bigger companies like Girl or Plan B have something.
It's also something that may possibly be negotiated when talking about a contract or something. I can see more financially valuable skaters possibly getting it or it may just depend on how good of a business man you are.
If you are a pro skater and you are paying out of pocket for an injury you get, then in my opinion that's your own fault. Just because your sponsor might not give you insurance doesn't mean you should get a plan for yourself especially if your job includes hucking yourself down stairs. Hell if my mother decided to switch flip back lip el toro and broke her hip, she wouldn't pay out of pocket to fix it. If you're getting a check to go skate, then not having health insurance to back it up is your own stupidity.