Aerodynamics is a black art, rarely understood, and if you think you've got a handle on it someone throws you a curve ball

I doubt that surfboards go fast enough for tip shape to have any effect whatsoever. My understanding was that an elliptical planform is the most efficient (like the spitfire's wings) but there are loads more factors in a windsurfing fin than just pure efficiency. Twist, for example, airplane designers put in a bit of 'washout' into their wings but that's for a completely different reason than why we put in flex and twist.
I think the only way anyone will get a handle on it is to build loads and loads of fins, test them all, and see which ones work. Slowboat, Decrepit and Le Sam seem to have done this, I'd listen to them over me any day