Alan,
The fillets on the sides of the cutter aren't a real problem, using a sweep with a profile that matches the cross section of the cutter should do it. The way I would do it would be to make a planar 2D path to drive the traverse and a projected curve used as a guide curve to drive the plunge. This will keep the sweep section perpendicular to the path, which is what it sounds like you want.
One of the problems with trying to simulate cutter paths in SW is the fact that you can't create features which self intersect. A cutter path done as a cut sweep will defintely overlap if you're clearing a face, but may be ok if you're just maching a groove or something.
The tough part with something like this is actually the flat bottom face of the cutter. If the cutter is ramping down so the axis is parallel to Z at all times, the bottom of the cut will be kind of scalloped. The face cut by ramping is not flat because the bottom of the cutter is parallel to the top of the workpiece, not angled at the angle of the ramp. This isn't impossible to make in SW, but it's difficult enough to hardly be worth the bother.
good luck