This photo shows the rudder assembly. The stuffing box isn't shown here. I took the photo when I was checking that everything fit before I re-installed the stuffing box. I labeled the components to help make it clear. The safety ring is pinned throught the shaft and the tiller arm is clamped to the shaft with a bolt. Both the pin and the bolted joint would have to fail before the rudder post could drop through the stuffing box.
The other thing you asked about was getting the prop shaft out of the boat. The biggest challenge I had getting the prop shaft out of the boat was that I wasn't able to get the coupling that connects the shaft to the transmission off the shaft inside the boat. It is a very tight press fit. There are techniques for pulling the coupling off the shaft, but I couldn't make it work. I didn't have the right tools or the patience to work in that awkward space. I ended up lifting up the engine and pulling the shaft out from inside the boat, rather than removing the coupling and sliding the shaft out through the bottom of the boat.
Once I had the shaft out of the boat I managed to pull off the coupling (using a pipe hammer technique). That is sliding a heavy section of black pipe over the shaft and, letting it bang against the coupling to push the coupling off the shaft. I heated the coupling to expand it and kept the shaft cool with ice water through the process. It took a lot of hammering to get the coupling off the old shaft.
I sent the coupling off to the company that supplied my new shaft to have it trued on the shaft and they said the old coupling inner diameter was too big to fit on the shaft, so I bought a new coupling after all that. They pressed the new coupling onto the shaft and balanced and trued it as a unit. I had a prop re-furbisher go over my prop (PropScan), and just installed it on the shaft after re-installing the shaft in the boat. I never heard of anyone balancing the prop on the shaft.
Take a good look a your stuffing box and the cutlass bearing while you have the prop shaft out. (or before you pull out the shaft in the case of the cutlass bearing.) I ended up replacing my cutlass bearing a few years after the shaft replacement and had to go thorugh a lot of the same steps over again. It would have been much easier to do it all at once, but as I recall, at that time I was dealing with so many projects, I couldn't keep adding one more thing or I wouldn't have gotten the boat in the water that season. Sometimes you just have to do as much as you can and take your lumps later.
Good Luck!
Chuck