I think we have to distinguish (as so often) between what we might like to be the case and what actualy is the case.
It would be great if we lived in a world in which individuals felt confident enough to present themselves in whatever gender role they saw fit, irrespective of the degree to which they conformed to the social/physical/aesthetic norms associated with that gender, and society was tolerant enough to accept them.
It would be great ... but that ain't the world in which we actually live.
The truth is that human beings are judgmental. For example, reecnt research suggests we make assumptions about a person's intelligence, trustworthiness and likability within tenths of a second of seeing their face for the first time. So this is a reaction that is hardwired into us.
Most humans also like to conform to the norms of their gender, culture, class, etc.
And finally, women are incredibly judgmental about one another's appearance: face, hair, figure, clothes ... it's all noted, assessed and ranked ... That's something that starts with little girls in kindergarten and it keeps going until menopause at least, and for some women till the day they die.
For all those reasons, the MTF transsexual faces an incredibly high barrier to acceptance. So being worried or even obsessed about passing is a completely natural and rational response to our actual situation in the world as it actually is.
My question, therefore, is this: when someone comes on here and asks, 'Do I pass?' what is the best, kindest answer? Many times I've seen girls who clearly don't pass being told that they do. The peopke complimenting them are, I'm sure, sincerely trying to be kind and supportive. They empathize with the person who's asking the question and they want to help. But is it fair to tell someone they pass when they don't?
By way of an analogy, I have a rule with my literary agent and editors, which is that I want them to be as savagely critical of my work as humanly possible. I like every possible criticism to be anticipated and dealt with. That way, when my work enters the public domain, it has the best possible chance of acceptance. I've learned the hard way how much it hurts when people in private say they love my work, because they're trying to be kind ... and then I get slaughtered by critics.
So might it be best to accept the harsh realities of life, and the 'hierarchy of passability' and give honest, tough, well-meant critiques in private, to prevent people being hurt (physically, sometimes) in public?