So like here's the deal: Yes, it's a bot vehicle. Yes, that means it stays flat when going up and down ramps. So I have a pretty silly idea in my head that sounds good to me but might be heinously handicapped to everyone else: I can bind the skateboard's ramp axis to the camera. Basically what that means is that the skateboard could theoretically turn as it goes up a ramp, but you would be controlling it manually by moving your camera up and down.
So basically you could do cool stuff like this:
But you could also do dumb stuff like this:
If this is interesting to anybody I'll work on it, if not I'll continue trying to come up with "alternative" solutions, but so far this is by far the simplest.