Modern four strokes can run really short skirts

partly because they don't have any ports to run over. Your old air cooled two stroke is going to expand and contract with heat a whole bunch, and it really needs the length of the piston skirt to keep the piston pointing up and down instead of rocking sideways. My guess would be that excessive wear on your piston skirt & bore allowed the piston to do way too much rocking even with it's long skirt on

. Try running it without the skirt and you'll shortly find those short skirt edges being hammered hard, and digging out chunks of your ports. Bore it out to the next oversize, install a new piston, pressure test it, and enjoy a nice melt-down free ride.