Well OK! I did a quick internet search on "Toureg tail light short circuit protection", and it seems many people have had weird problems similar to yours. The Germans do interesting things, and if they have put in some kind of short circuit protection in the light circuits, then I am out of my depth, and will have to withdraw much of my post.
You may find a physical wiring diagram helpful - where do the wires in the TM actually run?
Do you have what we used to call the blue book or blue binder? If so, there is a diagram of the physical routing of the wires and connections in the TM roof. If you don't have the manual, you can download it from the TM Technical Library, at
https://www.trailmanorowners.com/for...ad.php?t=13839
The various manuals are all very similar, so choose the Classic manual. Go to Page 42 to see the rear roof diagram.
You can see that the wiring goes from the refrig area, forward to the shell edge, up the driver's side to the roof, then inside the edge of the roof and back to the rear wall. At that point the wires divide and go to their individual destinations - in your case, the passenger side tail light assembly.
Since power is good as far as the refrig, the fault can be in the bundle that rises outside the trailer, as you suggested. Or the fault may be in the tail light assembly itself. I think it unlikely that the fault is elsewhere. In my opinion and experience, it may be easier to start looking in the lamp fixture, and break into the riser wires only if that doesn't work. Your choice.
In the absence of Germain engineering, the most common place for faults is in the light fixture. The fixture is easy to remove for inspection and testing, and easy to replace (with new caulk) when you are done. With the fixture off the wall, it is common to find that the ground to the trailer skin has become interrupted in some way. Ground is done with a wire from the shell of the bulb socket, either to one of the fixture's mounting screws, or through the base of the fixture and into a connector inside the TM wall near it. Look carefully.
The good news is that you don't have to break into the wires inside the rear roof.
Let us know what you find.
Bill