There is also a keyway to engage the coupling plate with the shaft.
The question is now I have loosened the stuffing box can I pull the prop shaft out of the gear box and hull with the propeller still attached? Is it OK to use a large punch to hammer out the prop shaft from the front of the gear box. Before I do any of this should the gear box be emptied of oil?
I had a diesel mechanic helping me for part of the engine removal when I converted to electric propulsion over five years ago. Yes, he used a large punch and a heavy mallet to knock the prop shaft back. Took three swings and it was done. We did not remove any oil from the transmission. We could not completely remove the shaft that day as the boat was still in the water. But, once the boat was on land I was able to remove the prop and shaft easily out the rear.
I replaced my stuffing box with a dripless last year. I have a Hurth v-drive transmission. I noticed a small leak in one of my transmission seals. To fix this issue, I needed to remove & send out the transmission for repair. I think you could damage your seals if you hammer way at the flange. Removing the flange from the shaft might require a lot more effort than a few swings with a sledge. The flange does not release from the shaft easily because the shaft is not tapered like the propeller end.I removed my flange with a heavy duty wheel puller and quite a bit of torque. Good luck.
Soak it well for a week and tap on it peridicaly. You will need a good gear puller to push the shaft out of the coupling. Most likely you will also have to cut the fiberglass to make room for the puller.
I have the same situation as Peter… Hurth V-drive transmission, I also replaced our stuffing box with a PSS dripless shaft seal and used a wheel puller to remove the flange… with the help of a punch and mallet to break the shaft from the flange, but the pressure of the puller with steady even force was the solution. You can completely remove the shaft with your prop still attached, be sure to remove any anodes that might be on the shaft forward of the strut and you should be good to go. Clean any penetrating oil off your shaft if you plan to install a dripless shaft seal as you should only use a mild dish detergent ( Dawn or similar ) as a lubricant so you don’t harm the rubber seal. I also replaced our cutlass bearing at the same time. Have fun.
My surveyor required me to remove the Paloma water heater from my Nonsuch 30. As far as I know, and according to the previous owner, it is in good working condition. If anyone wants it just let me know. If you pay for postage I'm happy to mail it to you. Otherwise, it is just going into the dumpster. (I am keeping the hood.)
I helped a friend of mine change to the PSS set-up a few years ago. We found it much easier to pull the shaft into the cabin after removing the prop, zinc’s and undoing the stuffing box.
The coupling at the transmission can be a bear. Just undo the four bolts to the trans and mark there position with alignment to the trans for reconnection.
I also agree that if the cutless bearing has any movement with the prop shaft, now would be the time to change it also.