CHB Trawler, 34' Rudder Removal Help!

I am in need of assistance regarding the removal of the rudder/rudder shaft, and a solution to properly repair a sloppy rudder to rudder shaft on an CHB Trawler, 34'. This rudder mounting is different from other CHBs that I have seen, in that the rudders are usually smooth and do not have any evidence of mounting the rudder to the rudder shaft. Not that it really matters for my purpose. This rudder/rudder shaft is loose/sloppy axialy, not much, but the boat is in dry dock so now is the time to address it. It appears that someone had previously attempted to rectify this issue by pinning and set screwing the rudder to the rudder shaft. In addition, although it is very difficult to see from pictures, the rudder's shaft hole has significant gaps inside, along the shaft length and between the rudder, maybe from corrosion or casting flaws. It is not noticable from the shaft entrance, as it appears solid and properly sized where the shaft enters the rudder. I believe someones attempt to pin or rivet the rudder to the rudder shaft didn't help because the rudder is not tight to the shaft for most of its length, and or possibly the shaft pin/rivet holes are slightly larger in diameter than the rivets. As can be seen from the pictures, I have removed the pins and set screws. The shaft should now able to be removed from the rudder. The problem I have is that it appears I need to slide the rudder shaft up by a little more than approximately 6-1/2" to be able to pull the rudder up and out for further inspection and repair. This does not seem possible without tearing up some decking to be able to remove two 2×2 wood supports. There is an upper shaft bushing mounted to a galvanized bracket which is mounted in between the 2×2 wood supports. The upper portion of the rudder shaft is supported and held up by the mentioned shaft bushing, the bushing is sandwiched between a castle nut and machined ledge on the rudder shaft so the shaft cannot move up past or through the bushing. There isn't enough room to move the galvanized bracket up or down and out of the way to remove the bushing. I am hoping someone has dealt with this or I'm missing something here. Hopefully the pictures I have will be of some help to understand my situation. I appreciate any help!

Welcome aboard. Sorry I have no info to help you but did want to welcome you.

I would purchase silicone bronze bolts the next size up and a tapered ream in the bolt size.

You might also need a NEW QUALITY drill bit slightly undersized from the new bolts.

A hammer would be needed for final assembly.

Rudder removal

I once had the rudder pushed up all the way when a travel trailer grounded the rudder. The bottom pivot popped out on its own. That was a 43 Albin.

I have a 34 CHB now and tried to remove my rudder to pull the shaft to change the stern bearing. My best guess was that I could flex the bottom arm down a little well pushing up the rudder, after removing the steering quad ect, and the bottom would pop out. I never did it because I pulled the prop and removed the bearing housing to change the beariing.
FYI the stern bearing holder (or whatever it is called) is removed by extracting the two studa and untreading the bearinmg CCW. It threads onto the stern tube.
A chap on this forum suggested I use a professional and I did that but he hammered for three hours smashing the stern tube, then gave me a bill for $ 500.00!!. Repaired the damage and finished the job myself.