I dropped mine in with the transmission and long tube headers attached. Radiator was out and hood was removed and sitting on top of the car. All the steering and suspension was still in place It went in very easily.
To add to it, it was done in my back yard, in the dirt. Car was up on ramps and engine stand was rolling on plywood.
If you want to, you can split the difference. Drop the motor in the car without the headers attached. But dont get it all the way installed. Leave the engine on the cherry picker and jack it up several inches and let it swing around. This will make it a lot easier sliding the headers down into place and getting them bolted up. Then when they're on, set the motor down.