I've enlisted the help of my non gearhead wife to do it. She works the hoist while I stand in the engine bay facing her. On the hoist I made an arrow with stop written on one end and down on the other end on the cylinder above the valve handle so there is no thinking involved. We do practice runs so she gets the feel for the drop speed versus valve opening position. Just to add insurance I use moving blankets to cover all painted surfaces and a piece of thick cardboard taped to the trans tunnel. The hood is off, the radiator is out, the front wheels are off and the car is jacked up and on stands just enough to let me slide under quickly.
Getting the angle of the dangle upon dropping is the most critical. As the hoist is moving foward, the engiine is dropping and foot pressure on the trans to send in into the tunnel needs to happen in a smooth motion. I put a flat cart at a position where when the trans contacts it it helps roll the trans rearward so you can stay up top guiding everything in.
Once in you can use a floor jack to slip under the trans, this might also determine how high the car needs to be raised so you can pump the handle. I put a piece of pipe insulation foam around the jack handle so as not to ding any paint. You can get this from any hardware store for a couple of bucks it comes in approx 4' lengths.
Fun times with the wife.