Now I understand more why you were trying to get center points for each rivet out of SW... are you using any tricks to generate portions of the code, or writing all the tool paths for a pocket strictly by keyboard?
I wrote VB programs, one or two of which you are familiar with, to speed up the recording process of lines, arcs, points, and freestyle elements into a SQL database and generating the G-code from that based on material being cut and the milling bit shape/diameter. But I take the measurements "manually" by offset-tracing the shapes in the model and recording the endpoints. On rivets, I just take the center of the hemisphere and use a ball point milling bit of the appropriate diameter. Then the CNC resembles a slow-moving embroidery machine, punching rivets.
For me personally the biggest question is what to do about CAD/CAM/CNC software when you're trying to run as fast as possible away from MS Windows. Getting three out of three is difficult for me on Linux with my lack of computing skill. Bryan's nod to hand-bombing code speaks to his skill set but that gets really tricky around organic shapes and ball ended cutters. I know it will get better with time as my abilities improve but at the moment it is a bit frustrating.
Keep in mind that, for the most part, I'm self-taught. Bob Fingerle explained the basics to me, and then it was trial and error after that. There are formulas to determine what the feed rate should be based on RPM and the material being cut and the diameter of the tool and the number of flutes on the bit that are pretty standard. Cutting depth per layer also is standard regardless of the material being milled or the bit head — ¼ the diameter of the milling bit. You also adjust the feed rate downward accordingly if your max RPM and/or top feed rate are lower (as on the Sherline) than the formulas suggest. But once you get the basic hang of it, it really isn't hard. And it becomes much easier to kitbash models when you can make precision cuts.
The more amazing aspect to me was that Bob was using simple two-part brass tools to make all of the American Limited products. They all pretty much followed the layout of the passenger car side tooling I thumbnailed above. And if there is a way to injection-mold polyurethane resin, then cutting tooling out of machinable wax really makes things easier.
