Rather than go to the effort of hooking up another trailer to try out, could you just test to see whether the voltage is there or not?
We all know that if the brakes are working, there is up to 12V present in the brake feed wire. No voltage, no brakes.
Perhaps you could get a 12V DC induction test meter such as
This one.Non invasive, you don't have to poke holes in the wires and find a ground to get a reading.
Leave all lights off, apply full braking from the controller, then go to the pigtail connector and look for a reading before and after the pigtail. The ignition key would likely have to be on, or the truck running. The tail lights need to be off for this. I don't know if your Ram puts them on by default or not, or if just the DRLs come on.
This little device has a feature that will show an internal breakage in the wire when you move it along.
It either has a reading, or it doesn't. You can easily check everywhere for voltage in the line by just putting the tip of the tester on the wire.
It's under 10 bucks, if you have Prime, you can get one in a day.
I think I may just order one myself!
And again, good luck to you, and have another beer for us! :B