Putting everything into neat little boxes will probably always be part of the human need to conform. Maybe it helps us when it comes to choosing who our friend or mate will be but it also severely limits our freedom to really get to know someone from the inside out. The neat little boxes are also important to those trying to shut out the unwanted from their lives, including those one perceives will do them harm. So I doubt there will ever be a time when labeling will be seen as unneeded.
I've looked at the gender stereotype question regarding trans people from the inside out and from the outside in. I believe initially we are trying to deprogram ourselves and then trying to find where we really belong, and we are using that which we've been taught as a guide. And we have to do it in a matter of year or two rather than over a couple of decades, the time non-trans people get to come into their own. So some slack should be given if we attach ourselves to stereotypes at the onset of our transition.
For me, I swung the pendulum as far the other way as I could. At one time I thought of myself as a girly-girl. Looking back, I now know I was trying to get as far away from the old presentation as I could, sort of as an attempt to get in the clear, so the smoke wouldn't cloud my vision. But in time the pendulum swung back and finally settled where I am today, a place where I am comfortable with who I am. And that is nowhere near the girly-girl stereotype.
Maybe the problem is the over-focus on the trans person at the onset of their transition. This is certainly the time they are most visible and when, for those who know them, the changes are most dramatic. I wonder how the general perception would be if the focus was on those who are several years past the time they transitioned. I think the findings would be very different.