At one of the groups I sometimes visit, there is a trans* woman who routinely has people asking her about her transition. She is frequently told how perfect she looks and how people would wish to turn out like her following transition. She's quite pretty. But due to voice, manner, and having had too much FFS, there are some very visible signs of being trans*.
I used to feel jealous about her.
I'm quite plain looking, and I'm certainly no beauty. When I go to that group (or other groups), no one ever says anything to me about my transition. But I have had people come up to me after the meetings to say they thought I was there to support someone else because they thought I was a cis ally. And the fact that I am the leader of a major regional trans* org has resulted in people thanking me for "doing exactly what an ally should."
When I started to realize how much this was happening, I stopped feeling jealous. She may be the one who looks prettier, but I'm the one who can travel in a space where everyone is assumed to be trans* and still have to out myself to people. There's nothing there to be jealous of and quite a bit to be happy about.
So I guess that means I'd rather be passable than pretty.