As promised I am reporting back with my cutlass situation. The reason the cutlass wore out so quickly is that the shaft alignment in the cutlass was off.
I did the following,
realigned engine so the shaft was centered in the shaft log
dropped the rudder
pulled the shaft and sent it out to the machine shop
had prop checked at same time
cut one side of the cutlass and removed it
installed new cutlass
used set screws to hold cutlass, did not drill and tap as factory install
while installing shaft I slid on new PSS shaft seal
aligned the coupling and the transmission flange to .005 tolerance
painted prop with Petit zinc shield, it was removed to check shaft
applied bottom paint to surfaces to be hidden by rudder
The centering of the shaft in the shaft log along with aligning the coupling flange with the transmission flange within .005 was the toughest part of the job. I will realign the flange and coupling after I launch and rig the boat for the season.
The shaft moves smoothly and easily with no binding at any point while turning it by hand at the prop. When the coupling alignment is out more that .005 you can actually feel the shaft bind as you rotate the prop through 360 degrees.
All is now good