I just sold an 1964 International Travelall that had a T86 with R 10 Overdrive transmission. I've been told the Plymouth Transmission with Overdrive is a better gearbox. I really liked the Overdrive feature especially with a smallish engine. (The IH had a 266 V8) There's a pretty good hill near my home which at about 3/4 of the way up would trigger the kick down. Once you crested the hill and lifted the throttle a little it went back into Overdrive. Getting it into 2nd gear Overdrive took the right situation and practice. I am sure most people wouldn't bother. A flathead Plymouth seems to be the perfect car for an Overdrive transmission. Overdrives have a certain charm to them and Plymouths are cruisers which amplifies that charm. If you don't use the "Automatic" feature of the B-W Overdrive, I think they are kind of pointless. In other words if your Overdrive doesn't work like it was intended automatically, I'd either fix it or get a different transmission. Using it to get "one more gear" is not enough to justify the trouble of having it. A T5 shifts faster, easier and has a synchro first gear. There's not much "charm" to a T5 though. I've driven foreign cars with the Laycock-DeNormanville Overdrive which are not "Automatic". You have to flip a switch or toggle a lever to switch between direct and Overdrive. Honestly, I'd rather have a 5 speed than a 4 speed with non-automatic Overdrive. L-D did not put the governor and kick down switch in because they figured the Overdrive would be engaged under full throttle most of the time. The L-D Overdrive was to be installed in sports cars, while the B-W was designed for full size American cars and trucks. Different designs for different vehicles and uses.
The freewheel feature should get some mention. First of all parking the car in gear does not ensure it won't roll. You've got to pull the Overdrive handle to lock the freewheeling. However, if you master it you can shift without using the clutch. You have to let the engine RPMs drop below the drive shaft speed to do it, then slowly raise the engine speed till they match then accelerate normally. I raced SAAB cars in SCORE Desert and Baja races. They had a dedicated freewheeling unit (it was a hold over from the 2 cycle days. Two cycle engines don't get as much lubrication when the throttle is closed, as the fuel carries the lube oil). I loved it as you could down shift going into a corner then power out without touching the clutch. I used it like a kind of "Pre-select". I suspect this has a limited application for a Plymouth as you will never rev one 7,000+ rpm. So the question is "Charm" and highway speed or modernity? You can put a V8 with an automatic in your vintage Plymouth and perhaps a front frame clip from something else for better steering and brakes, but what do you have afterwords? It will only look like a vintage Plymouth. There's something rather 2D about such a car. My choice would be the best example of what was available at time the car was made. That way it retains all of it's charm.