Yes - you could, I am sure, use a probe to measure the current diameter of a cutting tool, compare that with the current diameter stored, and either change the diameter, or change the wear factor. You could do this quite simply with a vis basic program.
The problem would be, however, where do you measure the tool from.
If it is across the flutes of a slot drill, then you must be sure that your measuring tool is a right angles to the flute, or you will get an incorrect reading. I cannot think of a way to achieve this with any certainty.
Perhaps the only way would be with an electronic type probe, which triggers when the cutter touches it, and you rotate the cutter at a fast speed and move the probe into it on a slow feed.