Although I like to sail, sailboat racing strikes me as fairly silly,
dunno why, it just does. However, my son has gotten interested in
paintball so maybe we can combine the two.......

Why not use mounted guns, port & starboard, (maybe a "chaser" in the bow too)
and count hits to the mast and below the waterline (assuming the boat is
heeled over) as "disabling" ....... sounds fun!! Now.... to make a paint-ball
cannon and grapeshot.......