I am thinking/wondering that removing the cutlass bearing would allow enough angle to get the shaft pass the rudder.
I don’t have a Hunter, but on my O’Day 322, the shaft was lined up with the rudder. In order to remove and replace the shaft, I removed the coupling from the shaft, and removed the stuffing box. Then I removed the prop and the cutlass bearing. That gave me a little wiggle room to get the shaft out and aa new one back in…I scraped paint off the rudder but got it out. Maybe the hardest part was getting the new shaft back into the shaft log.
If your shaft is bad anyway, far easier to cut it off and take it out in pieces. Especially if the coupling is frozen in place. I was trying to salvage my shaft, so I spent 2 days pressing the coupling off (just to inspect and decide to replace the shaft). The only problem with this is you won’t know for sure that you CAN get the new one back in…
But I think it was far easier than dropping the rudder.
Greg