It appears to be a dot product of a vector field and the curve vector (i.e. a line integral).
I think this approach can't handle certain cases where a path is retraced in opposite directions, like with the handwritten letter 't' or 'i'. Perhaps curvature integrals could be added as well to improve it.
I don't think so.
I draw my 9s by drawing the circle, and then the line down.
Looks like you go the other way. This is all about direction and gesture as opposed to OCR.