You can pull the OD section in the vehicle, but I'd pull the tranny to make it easier.
When you rebuild the OD section you have to have a 23 spline alignment tool to keep the splined sections inside the drum lined up. If you don't you'll never get *** together. The most difficult of doing it under the truck is getting the park pawl rod to go into the right spot. You'll likely end up pulling the pan, removing the VB and rod and installing them after the OD section goes on. After all that you might as well pull 10 more bolts and remove the tranny.
If you rebuild the OD section your self upgrade to the 48RE OD drum and stack as many frictions and steels in there as you can possibly fit. Buy the ATSG and make damned sure you follow the OD shimming procedure line by line. If you don't you'll have all kinds of issues and probably waste alot of time.
Sonnex makes some good 3/4 piston housing/piston upgrade parts that are worthwhile, but you have to tear the tranny completely down to install these.