I have pulled the tranny SO many times.... Just when I did the clutch - hopefully you wont hear the friction noise I heard......

Hears what I found, jack under oil pan (use wood), you will have to play with this angle and the tranny jack (i have the same HF).... You might be catching on the splines - if tranny is in gear and may work in N, give the flange a lil side to side (back and forth) action as you start to insert. After its in (keep minds outta gutter) you may need to give a pump or a release of the oil pan jack... once you have the right angles it slides in like butter.

I also thing I had the tranny tilted and angled slightly when inserting.
I pulled tranny and t-case as a whole.....
I pulled Xmember too - - and had the tranny jack on the tranny just infront of where the crossmember would go (keep this in mind cause you don't want the jack in the way when you go to bolt the Xmember on....

Hope it helps - take your time, get PO'd walk away and come back, it will fall into place.....