If only I would have read this about a week ago. When I pulled my gimbal bearing I noticed the same thing. But I never tried flipping it before I brought the boat in. I am convinced this was my issue. Kicking myself for not trying this. I had the gimbal bearing out and flipped it outside of the boat and had the same experience. I was so frustrated at that point i just didn't have the energy to do it installed. Dumb me. Oh well, it'll get a once over at least and hopefully be good to go when i pick it up.
Sorry for the late arrival, but just to share my experiences with something similar. . . In my less experienced days after replacing the gimbal bearing, I too could not get the outdrive back on. It stopped had maybe 3/4" short. I tried all sorts of things to no avail. It turned out that I had the gimbal bearing in wrong and it did not seat properly and therefore would not let the drive shaft go in all the way. I finally removed the gimbal bearing, flipped it around and re-installed it, making a world of difference. It seems that the housing of the gimbal bearings are slightly tapered in order to fit into the transom assembly ??? :noidea: