I do mine in neutral. This way the driveshaft is not likely to turn when you inadvertently hit the prop, cutting your hand. If the LU or the shift shaft come out of neutral before the LU goes back on then it's a problem.
don't use the bolts to pull it in; make sure the pin is in place correctly, the splines on the driveshaft are clean but lightly greased, then try rotating the driveshaft slightly to align splines while raising the LU. If not, figure out the mismatch between the LU gear and the shift shaft and fix that.
Should slide in with honeymoon fit.