I recently finished painting a surfboard using Molotow paint markers. It came out pretty nice, except for a couple of minor catastrophes, like where the bird pooped on it and the paint came off, or where the paint crazed when I sprayed glossy varnish. You can’t see the crazing from a distance, thank goodness.
Probably the best advice that I was given, and that I used on this board, was to “draw through.” Drawing through helps keep things believable. You can see it on the top arm of the octopus, where the arm goes up off the board and then comes back into view further down to the left. I drew out the whole arm onto my working drawing, and when I transfered the design onto the surfboard, I drew the unseen part of the arm onto the backside of the board.
Paint markers work really well on a surfboard – very easy to use and fun. I may do another one sometime.