Greg,
I don't think I took any of the flywheel and damper plate on the motor, but here is what I have:
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What you are considering could be doable. The tranny would need to come back about 6" or so to get the input shaft clear of the DP. You are going to have to lift the back end of the motor up pretty high to get the coupler clear of the prop shaft. The tranny is manageable in weight to get it out of the way so you can access the bolts (6 in total I believe) holding the DP to the flywheel. You might need to twist the tranny a bit (clockwise / counter-clockwise to get the splines aligned) when you are reinstalling it. (torque to 35 ft. lbs. when reinstalling) Don't forget, there is a flywheel housing bolt to the block behind the starter, so take the starter off too.
Good luck!
Harold