Tim,
What you are seeing in Lamar's Recess 2 file is one of the failings of the Offset setting in the To Geometry option in Extrude Boss/Cut. It is offset from the surface but the end condition is Planar; it does not adopt the curvature of the selected surface. :cry:
A method that will give you the results you want is to make your numbers as a separate Extruded part file. Cut/trim the extrude to a curvature that matches the desired offset, or depth of cut, of the face of your Recess part.
Then bring the numbers part into your Recess, position it where needed, and using Boolean Subtract, create the cut that follows the curvature of the Recess face.
It helps to create both parts relative to the Origin, then constraining the part for the Boolean operation is a matter of constraining the inserted part to the Origin of the part being cut.