When I took up the task on my boat, upon checking the shaft under the stuffing box, it was pitted. Not a lot but enough to concern me. It is a 1 3/8" shaft. So likely I could have just pushed in stuffing and let it go.
I chose to change the shaft. This made the job 100% easier. I sliced through the shaft. Removed the shaft through the stern - slipped past the rudder. Took the pieces to a prop shaft and had a new shaft made. The shop fit and faced a new split coupler flange matched to my transmission. The shaft was slipped back through a new cutlass bearing. The flange and the prop slipped on like a Michael Jackson sparkling glove. While I was at it I installed a PYI PSS drip-less shaft seal.
Now I feel confident that the structure will be solid for another 5 years or so.
If your frustration level has been reached this is a reasonable solution for a big payoff. My cost all in $1300 or $216 per year for a solid 6 years of service.
May I be so lucky to spend another 6 years sailing my boat in the glorious waters of the Salish Sea.