Glad it's working out well for you. I did install the wires under the tail lights in such a way that they come up from underneath the holes, however my suspicion is that the thickness of the wires caused the tail lights' rubber gaskets not to sit flush enough, so water still could drip in.
Anyway, I spent some time rerouting the wires through the bumper, and it turned out not to be that much of a pain. I found a way to pass the wires through the holes just under the tail lights and around to the side of the rear bumper using a wire fisher, and I only needed to unscrew the two 10mm bolts that are just under the tail lights, and the torx screws by the wheel well. See photos below for details.
One thing I made sure when re-installing the tail lights was to make sure the wires were out of the way completely, so that the gaskets could do their job properly when the tail light screws were tightened up. There was still play in the wire when I did that, just made sure to give them more space by pulling the weather stripping away a bit per the last photo.
I'll keep everyone posted over the next week or two if this was successful in completely avoiding water ingress.
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