I am both a machinist and a draftsman (and I had some designing too) and I know as a machinist, that that last dim that the CADs will not allow, is one that as a machinist, I have to calculate out and write on the print I am using. so where is all the crap about not allowing that last dim? It is crap. I'm not cheerleading for over dimming, not at all. Just that when a machinist has to pencil in a dim, then that is something the CADs and drafters should have done. So I agree with you, but often we mistake what others are trying to say.If it is a production set-up, a go/no-go gauge would be set up for that inspection operation. On aircraft, the inspectors had the gauges, and checked the holes to make sure they were in conformance with the print. They weren't expected to walk up, do a bunch of calculations, and then determine whether the hole met the specs. To do that with every hole would bring production to a halt.
As far as your example of a countersink. I wouldn't even use the tool illustrated. It's not even a precision tool, since there is no reference point on it, to set it from. It is for farmers and carpenters to make a countersink with. That tool could not be used to produce a precision countersink without trial and error, which is no way to produce a quality part. If you are going to take the time to do a set-up and test with that countersink, then take the setup down to drill the next hole, then set it up again and trial-test it again, you will soon learn why standardized tools exist. You can do it, but it will be MUCH cheaper and faster to use a industry standard tool. That's why they exist.
If you can show me a standard production countersink with a pilot that varies from every other standard production countersink, I would like to see the shop using it.
I have dozens of them, and they are all standard for their size and configuration. I can put the correct size countersink, in the correct spot, and know it will be right the first hole.
You can do things a thousand different, harder, more arduous ways. But why would you do them that way? If you want output, you will work smarter,, not harder.
The spec I gave you is still the easiest and fastest, and best to use. It's the one that should be on the drawing.
Again, making every viewer of the drawing do calculations should not be needed. If calculation is needed, it should be done by the designer, not left to the worker to complete the drawing.