You're replacing the cutlass bearing and the parts of the PSS.
Are you sure the shaft is in good condition and not worn in those areas?
I mention this because if the shaft needs replacing, it's a simple job to cut the shaft into pieces for easy removal of all parts.
Yes, quick way to get it out...but if the rudder has to be dropped to get a new one in, you want to know this going in !
On my O’Day 322, I was able to remove my cutlass bearing first, to get a little lateral play in the shaft, and pull it out past the rudder. It scrapped the paint on th rudder, but it came out. New shaft was also a tight fit to get past the rudder, through the strut and into the stern tube. Took some muscle and trying to bend the shaft a little to get it started into the stern tube.
But it all fit.
A few videos on removing these shaft,
Getting the old coupling off of the shaft (probably the hardest part):
Getting the shaft out and inspecting it (needed to be replaced):
Putting everything back together (always nice when a job is finished):
Greg