Hi Harnek,
In principle calculating offsets from an analytic "mathematical" B-rep surface is possible in most cases, and will give you an analytic solution for the tool-location.
However in practice there are numerical instabilities, not all surfaces are one simple B-rep, and the cutter-shape might not be a simple sphere.
For these reasons I think the pragmatic approach used by most CAM-packages is to triangulate surfaces, and then all algorithms can be written with triangles as input.
Currently opencamlib uses an analytic model for the cutter-shape (cylinder, cone, sphere, and toroid, or combination of those) - but in principle one could triangulate the cutter shape also.
There might be interesting algorithms for collision-detection between two STL surfaces developed for game-engines, possibly with GPU acceleration - this might be one approach for CAM also.
For the commercial algorithms unfortunately not much is published where the paper would actually state what commercial program is using the described algorithm - so it's quite hard to say what type of 3D algorithms are used currently by the popular CAD/CAM packages. Unless ofcouse you hear from someone working professionally with CAD/CAM - like perhaps the freesteel blog 10 years ago or so...
Anders