OD would be from the tip rather than the root, yes?
Yes please, tip to tip.
If you do all three, any uncertainties in the measurement will be minimised.
You are helped because they all have an even tooth count, so making the measurement is easier.
FWIW, I am leaning towards a dividing head-type application (helical/spiral milling) as they are all multiples of four. My feeling is that a ‘by fours’ sequence of tooth counts is more common here than in change gears.