50/50 deal if you've got a transmission jack
I've done it both ways. The disadvantage to installing the transmission on the engine is you need to be more careful not to scratch the car going in, and you definitely want a jack screw on you chain setup. Also Take the carb off and tape over the intake do to the severe angle your chain rig is going to be at. If I'm in a hurry this is the way I do it. Sometimes I'll just put a fleece over the trans to help ward off the scratches.
I don't mind help on the engine install but prefer to do the transmission install myself. A lot of it is just a feeling you get as it starts to go in. Two people make it dificult to get that feel.
As for doing them separate, I prefer to pull the transmission back away from the engine compartment. And definitely use a transmission jack. Drop the engine in and install the motor mounts and export brace, with the car on the ground. Sling the back of the block to the export brace with a truckers knot in a stretchy soft nylon 1/2" rope then get all four corners of the car up as high as I can on jack stands. I like the engine to have somewhere around 5-6 degrees tilt to the rear, that gives plenty of room to get to all the bolts, and the angle helps keep the torque converter fully seated in the transmission. Just a light touch of grease on the alignment dowls. The stretchy nylon rope will allow some wiggle room, and all should "pop" shut. Install the housing bolts with a 1/4" looseness, and make sure you can line up you flex plate to your torque converter. If your torque converter has a drain plug make sure it fits in the correct hole of the flex plate. Tighten the torque converter hand snug, then finish up tightening the bell housing bolts using a star pattern, like you would on a wheel. Do the same for the torque converter bolts. I prefer a torque wrench, even though I've done plenty. In fact after almost three decades of turning wrenches, my torque wrench still gets a whole lot of usage. Finally lift the rear of the housing up and install the rear mount then remove your rope sling.
Doing it this way, I have never fought an install. Maybe I'm just lucky, I've done more than my share though.
When I was young and stupid I'd lie the trans on my chest and bench press it into place with my head facing the rear of the car to help me align the transmission . Now I'm old and a little smarter. $90.00 for a transmission jack beats the heck out of a week off work with a bad back or dented ribs.
You can always buy some longer bolts or all-thread and make some long alignment dowls. I've never had to do this, but have heard others use it successfully.
Good luck!
Scott