Tim,
Airguy put an aftermarket headlight on his bike, IIRC he drilled a hole the same size as the hole in the original bucket and re-used the rubber grommet. The hole is on the bottom towards the back and slighly to one side. All the wires tucked inside-looked clean. I do not know if he had to rewire the headlight connector or not. I would think that you could find an aftermarket assembly that took the same type of bulb as the factory.