Chamfers on irregular edges

I am making a drop tray with a ragged edge (Montnana’s western border). Cutting the pocket with a ¾" bowl and tray and the outer contour with a ¼" endmill means the corners of the vector get rounded off. How can I get a 90° V-bit to follow the actual cut edges?

Offset the vector 1/8” outside. Then offset that vector 1/8” inside.
That should put 1/8” radius on all the concave corners.

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