Leaking issues in my 200 4R - any gurus available?

It's probably a simply thing and when you figure it out you're going to wonder why you didn't come across it earlier. But I know what you're saying about being frustrated!!
Unless you have a temp gage on the transmission you really don't know that it's over heating. If it's not over heating then it's got to be something else. I've been fighting an over heating problem on my daughter's '59 Studebaker Silver hawk for weeks (350 Chevy, all new everything). It's a new motor and have been broken in but I can't keep it from going over 220 degrees. I rerouted the upper hose, installed over full tank, new radiator cap, installed a high flow thermostat, added that additive stuff (wetter water??) to make it cool better, put blower fans in front of the radiator. I'm not sure what else to try so I ordered a new aluminum radiator and some high flow electric fans. Won't know till next week if it solves the problem. So, like I said, I know what you mean about "being frustrated"!!!
There's gotta be a simple answer!!!!

Treblig