Chooch you can probably go upwind but you need to bring that sail at 9 or 3 o'clock and using the paddle as a rudder.. If the sail is at 9 o'clock, the wind is at 3 o'clock and use your paddle as the rudder.jn a sense you are tacking at a 45-90 degree angle from the wind and just zig zag upwind to your destination. You have to use the paddle to steer the board.
I am ashamed of you Chooch .... you should have an EUC each side of the paddleboard... with a paddle tire... so the board can be like a little 'paddle steamer' (but electric) hahaha Awesome sail... and you have your cordless drill propeller for back up...
Yes I have had alot of experience with them. I had 3,000 dollars of damage done to my truck last year by one. I ran into one riding the euc one night. It was a baby and ran across the road and I cliped my pedal on its rear leg.