I was referring to the vertical drive shaft that goes into the motor not the prop shaft. I thought that it would be much more stable once installed into the engine, but was not sure if it could still wobble enough to allow water into the gear case.
I can not argue that a 20yo motor likely needs some new rubber seals! When I originally found the problem I traced it to the vertical drive shaft seal which had zero rubber remaining around the lower seal. I installed a brand new bearing carrier with the 2 seals already in place yet I am still getting water in the case.
I priced the new shift case, gaskets, etc and it was almost $70. I am hesitant to spend the $ if my parts are in operating condition.