All foils are tapered aft
The idea behind wing keels (as opposed to bulbs) is that the wings provide additional lift when the boat is heeled. All foils, of course, must be tapered aft. If you note the cross-section of the typical keel, it is blunt forward and tapered aft. Your main foil is blunt forward (the mast) and tapered aft (the mainsail leech). I don't know that keel winglets actually work. The trend these days seems toward bulb keels or the Scheel keel. All of these are trying to move ballast low, where it is most effective, while keeping draft shoal. If you aren't concerned with draft, the best keel is a deep fin. You can't avoid snagging stuff. The important thing is not to keep it, especially around the propellor. You don't have to worry about this, since you use an outboard (or paddles). I can imagine that winglets snag stuff more than simple fins. But I suspect this would be true whether they were tapered or square up front. It isn't worth cutting the wings off. The Hunter 23 needs every pound of ballast it has, and maybe a few more. Try to miss those lobster pots.
