Hi,
The bigger question is how are you going to actually cut the hole when machining?
I think you would be best modelling this the same way you would actually machine
it. Do you need an actual curved hole or will a hole cut into the pocket on the inside
join with a hole drilled from the outside?
If you are going to cut a straight hole into the side of the pocket to some depth, then
you would simply drill a hole on the outer face to join them. To get the holes lined up
you will probably need to set up a Plane at an angle to get the perpendicular or close
to it on the curves, and another plane that cuts the object at the depth you want the
hole.
The hard bit will be how deep can you make the hole within the pocket as the machine
tool will be cutting at right angles into the wall of the pocket. The hole from the curved
face will be just straight.
Cheers
Andrew