Just Replace Mine
Replacing the cutlass bearing is not too big a task. I just did mine a couple of weeks ago. I could not get the dripless collar off the shaft so I ended up taking the diesel loose and lifting it so I could pull the shaft forward out from under it. Even then I could not get the cutlass bearing out of the strut. I ended up unbolting the strut and took it home with me.After a lot of effort, I finally conceded that I was not going to get the cutlass bearing out without a more drastic measure. I put a hack saw blade through the bearing, put it back on the saw frame, and CAREFULLY cut through the bearing in two places lengthwise, avoiding cutting into the strut.Very little coaxing was needed to get the pieces out. Then I did a little cleanup on the inside of the strut, and the new bearing sliped in with only a little convincing from a small hammer and a block of wood. (Don't want to damage the new bearing by hitting it directly with a hammer.)Then it was a matter of slipping the shaft back through the dripless connector, slipping the strut over it, and reattaching the strut to the hull with some 4200 to seal it.I would also suggest checking the alignment of the transmission flange and the prop shaft flange when you are reassembling to be sure that there is not undue flexing due to a misalignment.Overall, not a bad job. My difficulty arose from the fact that the setscrews in the dripless collar had been installed with red locktite. I ended up having to drill the setscrews out and retap the collar for larger setscrews. Since I had to go through completely pulling the shaft, I went ahead and installed a flexible coupling at the transmission as well. (Only another $110, oh well.) Then I had to realign the diesel which took many trips between the quarter berth and the engine compartment....measuring....adjusting....measuring....adjusting...You get the idea.