I went through this when I first got my boat... when you replace the gimbal bearing you need to "set" it once it's installed. The "alignment tool" is what you'd normally use, but I made one by turning a piece of steel pipe down (on a milling machine) to the spec's that I found here on the boards... if it's aligned right, the tool / pipe should be able to is pushed easily into the coupler. You can make a sort of circular motion that will make sure that the inner portion of the gimbal bearing is not askew at all. If needed, then you can adjust the motor mounts to adjust the alignment of the coupler. When it's aligned properly and the pipe/alignment tool is centered, you should be able to slide the drive in easily.. I'm able to do it solo by adjusting the tongue of my trailer so that if I put the skeg on a piece of plywood, the height of the transom is correct to just slide the drive shaft in... if it won't go, turn the splines a tad and try again. If you're getting to within 3/4" then maybe the splines are aligned OK, but you haven't aligned the shifter tab correctly ? (look from the underside). Make sure the U joints are not sagging down into the bellows and catching you up there...
Good luck... I hope this helps....
I see the other guys are faster posters than I am... but we're all thinking along the same lines!