Have a pro model board or your own private park (like Area 52)?
Ooh... I'll take Pro Model for 500 .
Get a toilet-paper sponsor that pays you $100k a year, or ride for a boat company for free?
Toilet paper sponsor, no brainer.
Be able to time travel (without changing history) or be able to fly?
Compete in X-Games Real Snowboard or Real Snow Ski?
X-Games Real Ski
Barefoot in a speedo or wakesurf in a drysuit?
Wakesurf, considering my barefoot skills are not top notch.
Live in Orlando, but never get to ride on snow again, or live in Lake Tahoe but never get to win a wakeboard event again?
Win Masters water ski 3-event overall title three years in row or win Masters wakeboarding once and never win a wakeboard contest again?
I'd be content with one wakeboard ring.
Be a Michael Jackson impersonator for a year or have to listen to country music forever?
MJ impersonator all day.
Go bald or get a wakeboarding tattoo?
Win Video Part of the Year or Trick of the Year at Wake Awards?
Hardest one yet, but I'll go with Video Part of the Year.