Unfortunately not... GM changed the backing plate bolt pattern between the older drum brake and newer disc brake axles. The back spacing of the bracket is also different.
Do we know when the pattern/spacing changed?
Did all 14SF's go disk at the same time, thus no drum braked axles will be spaced right, or is just a vintage thing? I have only dealt with my 14SF, so I have no clue when and what changed over the years.
As to parking brakes, I grew up in a hilly area, and parking brakes were always used. It was how I was taught, and I am pretty sure everyone my age learned the same thing. I've got a manual transmission, and it only took hearing one story of an automatic trans popping out of park for me to realize that parking brakes should always be used. You can get away with it on flat ground I figure, but it's habit for me, just like putting on a seatbelt.
In the case of this setup, this should be a pretty easy swap with no e-brake, since the calipers aren't going to be expensive like the Cadillacs, due to rarity and complexity.

