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How do you measure the shaft length on your outboard
You don't measure shaft length really. Shaft length of just the height of the transom a given motor is designed to fit.
A lot of folks make the mistake of thinking that shaft length is the distance between the cavitation plate (aka...anti-ventilation, A/V plate, etc.) and the apex of the motor mounting clamps or "hooks". It is not. That distance will vary from motor to motor even within a given brand.
I have measured Long Shaft (20") motors that were as much as 23" and as little as 19-1/2" to the A/V plate. But they are both 20" shaft motors.
Yep just measure the transomif your checking Your boat. If you want to check a motor that us not on your boat measure from the bottom of the ears that set on the transom down to the anti cavitation plate. It will give you a measurement that will be close to the 25 or 20 inch measurement.