When Eliana was hauled out for bottom paint I checked the cutless bearing. It had a vibration that I didn't like and needed to find the issue and fix it. The estimate from the yard was a couple thousand dollars due to the labor to remove and reinstall the rudder and propshaft as well as the cutless. I did the job in 3 days, with help on the third to reinstall the rudder. The first day was removing the rudder and prop shaft. The second day was at home, constructing a tool to pull the bearing, and cleaning up the gudgeon. The third was to replace the cutless, and put everything else back together.
The first step is to remove the steering quadrant. Fortunately none of the nuts or bolts were seized.
Reverse all of this for re-installation. I used a helper, and ran the line up through the aft cleats, then forward to the winches. I slowly raised the rudder alternating winches while my helper guided the rudder.