you will need to dig a hole or...
do the repair while the boat is hanging from slings and up in the air. That's because the rudder stock is a couple of feet long and the rudder tip will hit the ground before you completely get it out of the rudder housing. You don't say if the boat is tiller or wheel steered. If it is a tiller it lessens some of the complexity of the job because you don't have to deal with a steering quadrant.I replaced the bearings in my old 23 challenger clipper a number of years ago. The "bearings" in this case were a couple of brass bushings which the rudder stock swiveled in. Don't know if the bearings on your boat are bushings or true ball bearings but changing them should be a pretty straight forward task. Just remember to dig a hole for the rudder to drop into or have the boat in the slings.Good luck,Mike