Re: cup probe
It sounds like you are trying to combine a tool setter with a touch probe.
There are 3 types of tool setters that I know of; Optical, a flat top switch type and a 3 axis system.
The optical is crazy expensive, the 3 axis system is almost crazy expensive, and the flat top switch is pretty inexpensive.
Let's look at the 3 axis system. It will measure the tool height and diameter, and is done with a flat top carbide ''puck'' on the end of the setter. Approaching from the top it will measure the height, and with the tool rotating backwards it will measure the diameter and location. You might be able to use this technique with the system you show above.
Jim Dawson
Sandy, Oregon, USA