I've struggled to refit an engine to a gearbox in the car for the reasons stated above. Much easier when they are both out!!!
My first experience was a 105E Anglia. We lifted the engine out with a length of rope but no hoist. I can't for the life of me remember how we did it, but there were no more than three of us.
Going back in took forever, The Anglia had a steel plate between engine & box and it just wouldn't mate up properly. In the end we towed it with an Austin Cambridge to a local 'facility' - tiled pit and hoist, and then it just slipped together. Looking back we should have bolted the engine loosely to the shell, but it didn't slip until we turned into the yard when it jammed the steering.
On another occasion three of us fitted a gearbox to an Escort Mk2 from below in a few minutes. The car was just on ramps at the front so it was very cosy underneath. I took it off myself and dropped it onto my chest - Escort boxes are not that heavy! It needed a release bearing.
