If you do a lot of these, I would make a fixture containing two dial indicators. The first dial indicator rides on the keyseat. The second dial indicator registers the end of the shaft. The fixture sits on a workbench or in a vise. You slide in the shaft until the first dial indicator starts to move, indicating that you've hit the end of the keyseat. Then you consult the second dial indicator to see how far you pushed in the shaft.
The reason that this is hard to measure is that when the keyseat starts to deviate from being straight, it has the same circular shape as your woodruff cutter. Because the circle it cuts is tangent to the straight line defined by the keyseat, the deviation Y from straight (what dial indicator #1 above shows) is quadratic (X * X) in the distance X from the place where the straight line ends. If your woodruff cutter is radius R, dial indicator #1 is set to read zero in the straight part of the keyseat, and dial indicator #2 is set to read zero where the straight part of the keyseat ends, then Y = 0.5 * X * X/ R. Suppose your woodruff cutter has a diameter of 1/2 inch, so that R = 0.25". Then here's a table
X (axial distance from where keyseat stops being straight) | Y (radial distance of curved keyseat from straight line) |
0.001" | 0.000 002" |
0.002" | 0.000 008" |
0.003" | 0.000 018" |
0.005" | 0.000 050" |
0.010" | 0.000 200" |
0.020" | 0.000 800" |
0.022" | 0.001" |
So if you make a fixture like this (or a jig that you can hold in your hand and put on a shaft while it's still in the mill) use a 0.0001" indicator for the dial indicator that rides in the keyseat, and a 0.001" dial indicator for the one that indicates the end of the shaft.
Alternative approach: have the customer to use a shorter key, or to add a feature on the other part which traps the key 1/8" before the keyslot ends.