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Beasho said..cantSUPenough said..
Being an engineer I was curious to compare it to the Rip Curl record of speed, wave count, etc. I think that the Rip Curl watch does not sample as quickly, so if you need to be traveling in a straight line to get the highest speed (which may be physically true too, but sometimes you know you are going fast with turns and it will score you a low speed).
I had surfing friends on 'prone' boards with Rip Curl watches. They would come back from the same session, same spot, same waves and show me their speeds.
They were ALWAYS slower. I chuckled and thought SUP's were just faster (re-read the above and not likely). Then Jeff Clark got a Rip Curl. We did closer diagnostics vs. TRACE and now are convinced the
Rip Curl reports 20% slower - All the Time.
Who wants that! So YES you need a faster watch.
YES!! Vindication!! 
(But are you sure it is only 20%

)
You have to wonder why. It can only be an error in the calculations. As per your explanation, to go faster you need to angle across the wave. Velocity is distance divided by time. The GPS
should give accurate distance. And a watch
should be able to accurately measure time.
But going back to your explanation, the greatest impact on speed is angle across the wave, but surely
a) the fin would affect your ability to make the best angle (like a sailboat's ability to tack up wind) - or is it the edge of the board that has the greatest impact?, and
b) the drag of the fin would impede the speed across the wave - but without surfing the same wave at the same angle with two different fins, it would be difficult to measure.
As for the proner's comments, I guess it comes back to the difference between speed (velocity) and acceleration. When you change direction, you have to decelerate and then accelerate again. But as you say, you never get back to maximum speed until you are zipping across the wave again.