The best location for a stern navigation light turned out to be on the port side, where the top trim was angled down from level. I wanted the navigation light pole to stand nearly straight vertical. The two choices were using a hinged pole, or adding an angled flange before drilling the entry hole. I thought the angled flange would be the better look.
I started with a compass, drawing a 3″ diameter circle on a piece of the Cherry wood I used for the top deck. The first operation was to drill a 1/8″ deep starter hole, with a 1″ Forstner flat bottom drill bit. Then I drilled the center out with a 1/4″ bit to place a 1/4″ bolt through.

After band sawing the circle, I put the 1/4″ bolt through it, and began spinning it with my drill against the moving edge sander. It created a regular circle, and I added a pleasing round over shape on the top corner.

Then I finished drilling the 1″ through hole for the post, and sanded the base on one side of the flange until it gave a good vertical position for the navigation light.

The mounting sleeve with cover was rotated to the best vertical angle, and screwed down to the deck. This bother is a detail that doesn’t get noticed often, but still satisfying. A sideways leaning Navigation Light Pole would always be noticed by some, and not considered right, if only by me.