Assuming your engine is a 350 TBI I'd go long block with new risers and manifolds.
You may want to take the extra step and have a closed-cooling system installed, less problems in the future plus it will help with resale on a boat like this since it already has bottom paint.
More HP on that 383 won't matter for wakesurfing, and most skiers would prefer TBI over Carb. Keep it as stock as possible.
I was njskier on here.