Colin,
I've dropped my tranny several times on my 3/4 ton. I think it will be much, much easier for you to drop the tranny and then install the engine, rather than try to "stab" the engine onto the tranny! Just drop the open part of the driveshaft by taking the u-bolts off the u-joints (9/16" open-end wrench, should take about 5 minutes). Then drop the TT by unbolting the cover flange from the back of the tranny (4 bolts, 1/2" hex) and unbolt the intermediate bearing assembly from the frame cross-member (2 bolts, I think they're 3/4" hex). With the driveshaft out of the way, you're ready to strap your tranny onto a jack and drop it out, nice and easy. Just my 2 cents- feel free to try to stab that 600 pound engine onto the fixed tranny from the engine bay!
Tyler