Evan I admire your persistence and wanting to figure this out. It's great to see the younger generation taking on these dinosaurs.
Your statement about your dad going along and his comments, plus it sounds like it's slipping now, makes me think it's time for a rebuild.
I think you are right. It's been hard for me to accurately asses and describe the issues the car is having with the transmission because frankly this car is somewhat of a basket case and have done a bunch a different work to it at different times in between the occasional short test drives in my neighborhood. I don't think its too far from being a good reliable driver though. Maybe a quick and painless Transmission rebuild is all it needs. Possibly even be the time to spice it up a little (shift kit) too match my dual exhaust, 4 barrel, and suspected cam work.
Again I have basically zero experience driving an old V8 like this, and don't have any gauge on how powerful it should feel. I drive a light little 4 beater with 4 speed (67 vw) everyday its the only car I've ever owned before this, my first. I've also only driven a hand full of automatic cars in my life, none of which were mine, and none were this old. That being said I've always felt like this one should feel quicker.
Come to think of it, from the beginning its felt like the car was struggling a little to move itself, and not because of the engine. And that I was just sort of being wishful a few times. It definitely has shifted somewhat normally a few times. I'm just sort of spitting stuff out here, its really hard to say given my lack of experience driving these cars.
At this point I know the engine is good, carb rebuilt, new plugs, wires, points etc
Finally got the shifter mechanism working properly a week or so ago
I know my drive shaft is good. Just had a new one made.
I know my motor mounts are good
I think my rear end is ok but really have no idea
I've probably spent about $100 so far on ATF. Once filled after park pawl housing replaced. Then I drained it completely more recently to put a new pan on it and added new fluid again. Ha!
I definitely need another person to at least try to drive it on flat ground because I'm lost on this one, and my dad has no idea.
I think I need to find a good trans guy that is local to me and have him rebuild it if that's what it needs. I have enough other work I want to do... just want it to drive good for now. So it can be a "running and driving project." I don't really want to just have a car sitting around while I try to learn how to rebuild a transmission. don't have enough time for that atm