Your pinion splines may be jacked, but this sounds like a more likely culprit. I didnt think the pitches on the nuts, even t-case nuts, changed over the years, but may have. If it strats fin thw first couple turns and then comes to a dead stop, then it sounds like the thread pitch is off.
Of course if you pinion splines are so jacked that you are having to drive the flange off with a hammer, then it is also likely that it isnt seating and the nut cant pull the flange down without more torque. If this is the case, your only issue is going to be when you get close to right on the sleeve as you dont want to ove crush the old one.
What year is your truck (sorry on mobile, cant see signatures). Can you pull the shafts and pull the whole third out? If you could get it out and on the bench, you might be able to tell more about it. If it is a 91 or 92, pull the rear cover and see if you can see anything inside the diff.