We currently have one vertical milling machine ( a traveling head shaper is being modified with the addition of a Bridgeport head, it's 2020 outside the door but more like 1900 inside ) which is worn out and big enough to stand on the table and machine the top of your head, I'm sure you'll appreciate using an 1/8 carbide endmill ( if we had one ) is going to result in roll pin AND the end of a carbide endmill in the hole. In 30 years I've only needed to drill out 2 roll pins, and one of them was to help someone else. Constantly sharpening drills may not be the best method, but it works with what we've got, if nothing else it means I'm working with someone else for a bit instead of my own.