Pushing in the clutch is probably only gonna make the clutch plate fall down and make it more difficult to install the tranny. The best advice I can say is to have everything line up as best as possible and wiggle that SOB and try and work the tranny onto the clutch splines. It could help to put the tranny in gear and turn the tranny over from the yoke to line up the splines with the clutch, once it gets close enough it will require a little play with the hoist to keep the tranny level. Then you can install the bolts and start tightening her down to suck up the slack. If you have to force it to far something is still misaligned. When I reinstalled mine it sucked up pretty close so that it was on the splines, but had to be raised and lowered a little before finally getting settled properly into place.

Hope that helps.

Jeff

My 1953 Chevrolet
1947.1 Gallery
1972 C-10 1/2 Ton & 1972 C-30 1 Ton