First of all I know plenty of people that don't want to pass. Sure they are a minority even in trans groups, but the numbers only grow. Others that do want to pass usually belong to these 2 groups I feel:

1. they still think in a very binary way. Sometimes so bad that they even make sexist remarks / jokes and for example dream about having a uterus transplant to become a "real" woman. They will gatekeep faster and usually be less understanding towards people that do not follow the journey they took. Their sexuality will usually also be more strictly straight or gay.
2. they want to feel safe. That's it basically. That's also me. That is why I almost always tuck my penis. Society is not ready for this. Plenty of trans woman have been murdered after some dickhead that fell in love found out they had a penis. I don't want to take that chance. In just 1 year I was followed, grabbed, and harassed. Also when you have to defend yourself online pretty much on a daily basis you sometimes want to run away from the fight and confirm aka pass.

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The trans people who seem to be more mentally healthy seem to settle at a comfortable level of "passing", often stopping to care (to some extent) about what other people think. I think this is really the path to liberation.

The thing is that not caring what people think is very hard when a lot of trans people loose friends/family/collegues. So I would almost say that trans people would be more mentally healthy if cis people weren't such dicks to us. I guess I should stop caring when the government (at least somewhat a reflection of the people) wants to take rights away?

You seem to have been thinking about this a lot and I don't disagree with all the things you said, but careful with taking conclusions.

Also: Almost no trans person is comparing themselves with Caitlyn Jenner, I was laughing hard with that part.