I am at best a mechanical hack so take this as you will.
I doubt it. The bell housing and the oil pan don't play together nicely. When reassembling my 59 AB, I tried to install the bell housing after the pan was on - didn't work.
Your mileage may vary.
I dropped the tie rod, pulled the starter and removed the crossover pipe. Straight uneventful drop. Lifting that sucker back into place was the difficult part.
If you're by yourself, you might consider some Felpro "snap ups" they screw into the block and allow one to seat the pan until bolts are installed. Come 4 to a kit, plastic and pretty durable. Best of luck.