1968 Dart 273 - Freeze plug replacement

i've used that style tool to install them in-situ. the job is decidedly not enjoyable.

personally, i wouldn't gamble and that motor would be out and on a stand to to that job and a reseal on the rest.
Since you have experience with using the tool in car,do you have any tips or advice as to do this the most easily? Unfortunately I dont own an engine hoist or stand at the moment. If I did and went that route id also replace the rear main seal even though the car doesnt leak.