Smog mercedes 300E
 

Will the car pass smog with a leak in the head gasket if the oil is NOT milky

Not really any way to know that other than to try it. There could be other things wrong or out of adjustment too that would cause a failure.

I would think it depends on which way the head gasket is leaking. If coolant is going into the cylinders, it most likely won't pass because of the obvious white smoke and weird emissions that will produce. If it's leaking oil to the outside, I wouldn't worry, mine has been doing that for 7+ years and passed every New York inspection (finally getting that fixed this month). Oil into coolant, it may still pass.