Extruded Cut Along Multiple Contour Faces

Hello, I'm trying to draw a brush.  The bristles need to be mounted on an "arm" (like a wire brush), but the arm is contoured instead of flat.  I need a small circular extrude cut in the arm for each bristle, and then I need the bristle to stick out 1" from the surface. 

Since the contour isn't finalized, it is easiest for me to draw the contour on the front plane, close the sketch, and extrude to the right width.  I then tried to draw the bristle cross section on the right plane, run a linear pattern, and Extrude Cut Offset from Surface, but that only works for one surface (my face is a combination of several).

The only other thing I can think of to do that is not incredibly manually intensive is see if I can do a linear pattern on the contour sketch to offset it - say, 1.1" -, somehow get my bristle cross sections to pattern along the contour, and then extrude 1.1".  That still doesnt take care of the cut though (want it to be close for weights and balances).

Any ideas?  Advice is awesome, too, somehow I got stuck doing our production designs and my boss thinks mine are cartoons

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