I know it might be tough, but it will help to have one person pushing the L/U up while another person "jiggles" the flywheel to get the driveshaft to sync, that would be my first thought. Did the shifter get moved? I know it is tough to get the water pipe lined up along with the shift shaft all the while holding the heavy piece up to get it into the housing but the only things that could stop it up would be the driveshaft splines or the shift-shaft splines binding up or not mating exactly to slide into each other, those would be the only 2 things I could think of.
I cracked my shift shaft where it mates into the splines, like as if someone sliced a carrot top at an angle. I had pushed the L/U up enough to get nuts on the threads , I kept torquing the nuts wondering why they were so tight, well the shift shaft was not aligned and all the pressure chipped a piece right off. I was able to JB Weld and along with a S/S clamp it broke off so clean that I was able to just glue it together and got it to work for the next 10 years but I learned my lesson after that, if the L/U doesn't easily go right up into that housing, drop it and rotate the flywheel or have someone rotate it until it slides up nice and easy. I had my girlfriend do it for me this past December when it hung up for a moment and thank goodness she was there or I would have had to move the flywheel ever so much every time to get it to mate and it would have been a pain. Good luck.
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