This is all subjective and depends on the individual.
FalsePrincess is right... it's a (usually) *very* slow transition from male to female. Both for physical characteristics, and mental and behavioral characteristics. If you're doing well, the behavioral change is ahead of the physical, so the moment you appear questionably female, you're mostly there.
LTL, I think your issues with passing as a male should be a pretty good indication of where you're at. Can't wait for the day you take the plunge. It's not as hard on the other side

, especially for someone pretty like you.