shouldnt bobcad keep the toolpath within the boundary instead of using it as a center line for the toolpath...
i would think the toolpath should be 1/2 cutter diameter inside of boundary.
is it also going to wipe out the details within the boundary by half the cutter diameter.

Offset the boundary in by half the cutter diameter.
v21 has option to contain to the outside of tool, v22/v23 does not.

edit: This is a prime example why you should almost always pick the whole model as the Geometry. If the boundary doesn't contain the tool correctly, worst that will happen is the path will climb the adjacent feature.

I got your file and will look at it soon.

moldmker