I did get a little deeper into the rudder shaft issue today. I have all kinds of penetrating fluids working for me. I believe the top “bushing” is free as fluids pretty much drip right through onto the quadrant. But the bottom/hull seal appears to be a different story. You can see in the pictures that the bottom seal was originally a packing gland wrapped by the orange colored hose. Above that is the bottom side of a flange in which I believe packing rope got sandwiched by a second flange that slid down from above and bolted to the lower still visible flange. This made the watertight seal. Unfortunately the upper flange snapped into three pieces upon removal.
Are you able to dig out the "packing rope" it would make it easiser for the oil's you are using to go further down.
Regardless, with the upper part of the seal now broken it would appear I am either looking at finding the original flange (where does one order these things?) or upgrading the whole thing with an updated rudder seal. Hopefully I could find a replacement seal that fit the bolt pattern on the hull thus avoiding having to rework the hull too. Either way I am looking at dropping the rudder in order to get the flange or new seal in place. So I still have to deal with whatever is frozen in order to drop the shaft.
I am not discouraged. I was prepared for this kind of job and had already adjusted the purchase price. Plus there is nothing like hanging upside down in a lazarette for 4 hours to help one learn one’s new boat.
I am still attracted to the idea of heat. That might loosen things. Also I can access the top of the rudder post yes. However, I think there is a pin in the top of the shaft somewhere holding it all up. I am having trouble locating the pin. Once located and removed I may give her a few gentle taps.
See photos for details.
You must drop the ruder so you can inspect the rudder shaft.
I would start by dismantling the parts you can get access to.
The rudder quadrant must be taken off, seems to be made of aluminium.
Gentle heating with a torch can help release the SS bolts.
The ring in your picture between the stuffing box and the quadrant - do you know what purpose it have?
If you have to replace the stuffing box and bearings I would look at alternative solutions.
New solutions have been found since the boat was new
Here is a company with info on different solutions.
Jefa rudder and steering systems
direct link to an upgrade
Converting from plain bearings to roller bearings
Here is alternative solutions to get a seal