I sharpen the same number of strokes per tooth as a somewhat close estimate. About mid way through a chain I will take a hard look, sometimes with dividers or a magnifier headset, to see how the individual tooth lengths compare. Generally I find one side shorter than the other, but I've been correcting pressure some. If I find the my dominate side, my right, is noticeable shorter then I take a couple extra strokes off the long side.
I use a bench vice to sharpen for a couple reasons. The work is held steady. The work height is comfortable and I can move with my legs, holding the file fairly consistent throughout the length of the file stroke. And relating to eyesight, the lighting is very good.
In the garage or out in the field same process. I run the file until i see or feel the leading edge just start to curl and then I know it is time for the next. It is rare that one side of the chain is longer, but when I notice it is loped side I do the same just a couple extra strokes to let the chips fly Thanks