In an article in REFERENCE on rub rails at
http://continuouswave.com/whaler/reference/rubRail.htmlthe epoch of the change to the two-part or three-part rub rail with vinyl insert and plastic receiver track was c.1972.
Perhaps a reader with a post-c.1972 MONTAUK with the new-style rub rails can provide an illustration of the location of the navigation lighting wiring box in the stern of the boat.
I would expect that the wiring would NOT be bent around the stern quarter at the transom and lead across the transom, as that would put a big bend in the wiring, expose that wiring to damage if the hull corner hit hard against something, and put a hole in the transom at an import point of strength.
On my 1976 SPORT 15 the wiring was run through the hull about a foot forward of the transom. The wiring was on the Port side. In the FAQ on navigation lamp wiring, which you will find at
Q4: How Do I Repair the Wiring for the Combined Sidelights at the Bow?
http://continuouswave.com/whaler/reference/FAQ/#Q4the method is described in more detail. When drilling a hole from the outside of the hull and drilling through the rub rail receiver track, I would probably angle the drill downward so that the exit of the hole through the cockpit gunwale or inwhale was lower than the height of the rub rail, that is, I would NOT drill that hole from the rub rail receiver track perfectly level into the hull so it exited right at the same height. At least, that is what I think I would do. Take a close look at the hull and see if that makes sense.
Here is a view that appears to show a MONTAUK with the navigation lighting circuit terminal block on Port, near the transom, about 12 to 16-inches in front of the transom:

Here is another view of a MONTAUK, and it shows the electrical box on the Starboard side, also ahead of the transom:

Note in both views the height of the electrical box is significantly lower than the rub rail receiver track center. I think you will need a long drill bit to make this hole. Again, a call to Chuck Bennett may provide more details.