On the old group we had a long discussion on ways of removing the cutless bearing. I remember three. One was to remove the rudder, pull the shaft, reach in through the bearing to its forward edge and pull it out. The second was to remove the prop, grasp the small projecting edge of the bearing with vice grips, and pull the bearing out. The third was to pull the prop, dismantle the shaft packing and with the packing out and the nut slid up to the coupling, insert one or more short pieces of pipe split in half lengthwise down the side of the shaft and push the bearing out.
I just had my cutless bearing replaced at Sailcraft in Oriental, NC. After pulling the prop, they tried the vice grip thing without success. They then took a hack saw and cut two small knotches in the opposite sides of the projecting part of the bearing. Then using a tool like the bearing separator (McMaster-Carr item 6342K1 on page 1137), they grabbed the bearing by the two knotches. They then used two jack screws inserted through the holes in the bearing separator (marked C in the McMaster catalogue) to pull the cutless bearing out They used two scraps of steel plate to pad out the fiberglass under the jack screws to avoid marking the fiberglass forward of the prop. This method worked like a charm taking abut 5 minutes total. To make it easier next time, they cut a 1/16" grove around the projecting end of the new cutless bearing on a lathe before installing it.