well, the way I see it is that in both cases, air resistance will be constant, so you can't really consider that (whether you're flying through the air, or on the ground, air is still there).
I don't think there's a way to prove this, but my hypothesis is that the guy that stays tucked and rides all the way down will get to the bottom first. Simply because, if you were to straight-line a hill, you're pretty much accelerating down the hill constantly.
Now if one was 'jumping' (or ollie-ing, right?

) you'd be interrupting this constant down-hill acceleration by applying a force downwards and thrusting yourself upwards. Granted, when you are 'falling' from your jump, you'd be accelerating faster than if you were on the snow, but the constant thrusting upwards would keep limiting your speed, imo.
Honestly, the ONLY way to truely know is to test it, since there really is no formula or way you could prove this with theory.