Been thinking about the pilot more. If I want to make it with a standard end mill I will need two separate setups on my mill. With the piece held vertically in my RT there is no way to cut the "vee" and leave the pilot fully intact, so I would need to hold the piece horizontally in a vice, then transfer it to the RT and line it up so I can get my 15 degree relief. Doable but a bit of a pain.
However, if I happened to have a Woodruff cutter the right size (I don't) I could probably machine the vee and relief using the RT. Something to think about though.
Even if I give up on the goal of getting exactly 15 degrees, I can't just grip the piece vertically and machine the relief, because it will be about 2 inches above the vice and the diameter of my homebrew CS will only be 3/8 inch. That is a recipe for machining difficulties, to put it mildly. The RT+chuck can accommodate the full length of the piece so I can grip it just below the vee.
I I thought I would be making more of these I would go ahead and make a fixture to facilitate their manufacture, but right now I don't see the need. 99% of the time the holes I want to countersink are accessible with a standard CS.
Pontiac, I've got a question for you. Looking at the photo in message #3, it looks like you cut a relief on both sides of the "vee", but only one of them will actually cut. What is the purpose of the other relief cut?