I replaced the cutlass bearing on my 8.7 last winter. I don't know the differences between the 8.3 and the 8.7 so some of this may not apply. It is a big job. However, I had to pull and replace the shaft any way so as long as I was that far into it I replaced the bearing. I had thrown the shaft on the way into winter storage and bent it. As the boat was being hauled I had them take it as high as possible on the travel lift. That allowed me to drop the rudder out without having to dig a hole to drop it into. Then, while on the stands I pulled the shaft and replaced the bearing. Hint: the bearing is a simple jam fit. While you are at it repack your stuffing box. Carefully check your engine mounts for cracks. I had to get 2 welded. Then reverse the process. Hint: get a set of extra long bolts for the rudder post flanges. We had the boat back up on the travel lift when we realized the old bolts had been cut to fit after compression and needed longer ones to catch the thread. The yard manager was totally pissed when it took 2 hours to locate the bolts and we had his lift tied up on a busy Spring Sunday.
BTW, anyone know of an 8.7 that is being scrapped. I need a pair of the stern chocks.
Good luck with your shaft bearing.
BTW, I just started a 3 plus week solo cruise around Door County WI. The weather is fantastic but it took 25 hours under power to get up from Chicago in a north wind.
Chi Lin 8.7 # 179