You mention Powerglide transmissions. I'm probably the only one in the world that doesn't like the 2 speed transmission. In my opinion, Chevrolet was asleep at the switch for years. In mid to late 50's, into the mid 60's, Cadillac, Olds and Pontiac, all had 4 speed automatic transmissions. I drove my father's Cadillacs that had these 4 speed transmissions in them. To me, a world of difference. Chevy was very late to the party on this one. I guess it probably had a lot to do with cost, but eventually, they came around.
You might want to keep your car original as I do my '55 Belair vert. I respect that decision, but if it wasn't for that, I would have changed mine out a long time ago to an overdrive transmission. If I don't start or drive mine weekly, it pukes fluid all over the floor. Tired of cleaning it up. And to me, it's just a lame transmission. My car is a 265/162 hp and needs all the help it can get. I read that the racers like them, but I don't race. Best wishes with yours, Carmine