Any cooler is better than none. As someone mentioned before, it is possible to overcool a trans. With a non lockup converter like what’s in a 400, it would be very difficult to overcool a non lock up trans.
If you look at the cooler flow diagram of a 700/4L60, you will see the cooler flow is restricted while the converter is locked. That’s so when your driving on the interstate with the outside temp -10 below zero, the trans doesn’t get too cold. Most of the heat in a transmission comes from the torque converter.
Ok, transmission cooler lesson is over, class dismissed!
Install a cooler, keep the radiator cooler also. If you plumb the auxiliary cooler ahead of the radiator cooler, then the radiator cooler will keep the trans from getting too cool. It might also help the cooling system if the engine normally runs warmer than desired. On the flip side, if you really work the truck in the heat, at low speeds, then the cooler after the radiator would probably be best. That way, the auxiliary cooler can radiate extra heat before it gets back to the trans.
Lastly, if you don’t already have one, a deep pan is a big help. The deep pans hold an extra 3 quarts (I think) and are a simple bolt on. The factory deep pan needs to longer filter tube, longer filter bolt and extension sleeve. Aftermarket deep pans will include everything needed to install.