I like your system I would have like to have seen the rope wrapping around the device when you pull the sail out. I just am wondering how the rope wraps upward.
assuming it's a sea kayak, you're going to heel (lean) a lot from the wind. Your kayak is narrower, while the sit inside design won't let you hike (counter-lean). So you'd need outriggers or 'side pontoons' although they don't have to be big.
