My May 2022 posting on how I removed my rudder, (search Barbour rudder) might give you some ideas.
To lift the rudder, I made a fitting to screw onto the top of the rudder so I could pull it up using the main halyard
Getting the rudder shaft to enter the top bearing was frustrating. Finally I used the emergency tiller to wiggle the shaft around until it finally entered the bearing
John Barbour
Nonsuch 26 Nature
Toronto