I think your saying to check if there is too much grease (causing kind of a suction lock), I'll double check that, but it doesn't seem excessive to me. The alignment still doesn't seem perfect to me, and not as good as it was before replacing the bearing. I had to tap the alignment tool into the coupler the last inch or two with a hammer to get it to fully seat (this is mainly why I think that's my problem). I did give the alignment tool a few moderate whacks with a hammer in each direction as well (sides, top/bottom, but more so the bottom as that appears to be the angle that's binding). Once it was fully seated though it spun freely. When I was installing the outdrive, and got stuck the last 3/4", I tried the Mer-Kick method of a few good kicks on the back of the outdrive. This did not get in any further though, and it basically stuck where it was. I actually couldn't get it back off by hand and had use the method of reinstalling the trim rams and a block of wood on top, then raising the trim to pop the drive back off. So, that too seems to indicate to me sort of a friction bind in the coupler/splines (meaning the splines are partially engaged and aligned rotationally, but misaligned longitudinally) due to slight misalignment. Meaning, if it was just stuck on a lip or something it should have come right back out easily, but sticking in place i can picture the driveshaft may be getting jammed that last 3/4". I'm pretty leery of using the nuts/bolts to suck it in, in my experience with transmissions that's usually a good way to ruin things.a couple of things that have hung me up when almost all the way in - the orings on the driveshaft- are these greased up, and when I have been doing alignment work one can build up a lot of grease in the coupler and take some effort to squeeze out.
Did you check the alignment i ok? While it doesn't have to be 100% textbook perfect, just that the witness marks of grease are reasonably even around it. My current boat was never able to get full grease on the bottom of it, further adjusting just took it farther away... Still on the original gimbal and coupler at 20 years /450 hrs...
If so I have had to give it a good foot shove or lightly ( by hand with very little force) use a rachet and the nuts to get it on. Shouldn't take any real force, just snugging it down with a calibrated elbow