I am by no means an inline board expert, I do know a cross wind or trolling parallel to the waves will cause the boat to "slide" sideways. My boat sticks out of the water a lot more than that tiny board, and a cross wind will push the boat sideways much faster than the board, the line gets a bit slack and the board drops back.
The up wind board on the other side pulls like a rented mule as the boat "slides" away from the board. The "slide" sideways can be considerable, and being out in open water, we don't even notice it happening.
Just my $.02 from an old guy..