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With respect to the O rings, you are supposed to use only motor oil on them. I'd make sure there is no grease in the grooves for the o rings. Then oil them, put OMC triple guard grease on the driveshaft splines. Even if the engine is properly aligned, this can be challenging. You are dealing with the difference in height and angle of the pivot housing (where the drive bolts on the transom mount) and the drive itself. So the challenge is to get the pivot housing and the drive at the same height and angle relative to each other. THEN, to keep the driveshaft/ujoints straight when you guide the drive shaft through. I try to get the boat level ground. Then get the vertical surface of the pivot housing 90* up and down. Next use the alignment tool to get the gimble bearing straight in the gimble housing (it can tilt, a number of degrees and that can get the driveshaft off from where it needs to be for it to go into the coupler). I use this stand, sometimes I put a scissors jack under the front of the lower unit, to get it just at the right angle. I put a piece of wood across the bottom rails and put the jack on that. When the angle is right, it goes right on. If not it can fight you for a while. Sometimes it'll slide almost all the way on, but not go all the way. If I give the scissor jack a turn or 2, it will lift the drive just enough to make the driveshaft slide into the coupler....
