I went ahead and run the wire along the roof rack, into the channel from the factory rack rails (via a drilled hole), forward and out another hole. It then drops though yet another hole in the rain gutter and inside on the top of the door frame. The wire gets pretty mashed but it has a beefy jacket. I'm going to have to keep a close eye on it. If it turns out to be wearing, I'll just drill a hole in the roof and route a new wire.
On the subject of roof rack mounted lights, I didn't feel like paying $30 for Garvin's light mounts for the Wilderness Rack. I made mown out of a section of 2" square tubing. It was quick and easy and works great.