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It's possible the load on the shaft caused the stuffing box to distort and go slighly out of round which will make it difficul to remove the shaft.
One time I jury rigged a tool to remove a sticky rudder using two 2x6 blocks as shown below.
One block has with a hole drilled large enough to go over the stuffing box. To use this approach, remove the packing nut and the timber that supports the rudder bushing. The timber is held in place with a couple of lag bolts.
After removing the timber and the packing nut, drop the block with the hole down over the stuffing box. Replace the packing nut loosly so it doesn't bind on the shaft, but prevents the block from lifting off the stuffing box. Place a second block on top of the shaft and use bar clamps (or threaded rods) to apply pressure to the top of the shaft, pushing it down through the stuffing box. You can develop a lot of leverage with this technique, and you will need all of it if the stuffing box was distorted when the shaft bent. (The cross hatched areas in the sketch represent the fiberglass hull.)
This approach doen't transmit any load to the hull itself. You are pushing the shaft directly through the stuffing box. If you have access to a machine shop and can replace the wood blocks with structural steel, that would be even better.
Good Luck!
Been there, done that!
formerly
Lots A Luck
Trojan F-26 Express
Narragansett Bay, RI
I had no luck with the liquid wrench and dead blow but I just found a whole drawer of miscellaneous pullers in my shop. Operation "Bent Rudder Removal" continues tomorrow!