He is depressed because he is trying to be something he is not, and deep down, he knows it.
Sandeen is the classic crossdresser who gets bored and tries to become a transsexual so he can keep the thrills going. The classic example of this was Renee Richards, who tries, desperately, to deny that he made a mistake, even though it is clear that he did, and that he knows it. I have suggested to several therapists that they read Richards' book to better understand what should be red flags indicating that a person should not be considered for SRS. Such an intervention might have helped Sandeen who shows much the same sort of history as Richards.
On a certain level, it feels like I’m internally fighting for my survival as a woman because of external efforts to define me as a man. And internally for me, this is at the intersection of being a trans woman and being disabled due to mental illness.Of course, Sandeen is not a woman in any sense of the word. He is a male-gendered, male bodied person who is trying to rebel against gender norms. He cannot change his brain, which is clearly and immutably male. He has not remotely changed his body to be female (though that would just make him what would effectively be a sort of pseudo-FTM. We have more than a few of those already.
Like most men, Sandeen refuses to admit to error. He has chose this path, and he intends to stubbornly see it through. I suspect his castration was motivated by a desire to prove that he was man enough to become a woman, making a sacrifice that would upset a lesser man too much.
Sandeen cannot "survive" as a woman, since he isn't a woman to begin with. He cannot be what he is not. And deep down, he really does not want to be. He wants to be a "gender rebel," like "Kate" Bornstein, another highly disturbed individual who mistakenly thought surgery was the answer to his demons.
Those external efforts that Sandeen complains about are called reality. He has a penis. He is a man. End of story. He has attempted what is, effectively, a legal fraud and he committed perjury to accomplish this. He basically lied and claimed to have changed his sex, when he has not. When he is careful, he speaks of "legally changing his gender," which is an absurd idea.
First off, according to the way that Sandeen would normally define the word, it is neither a legal concept, or subject to change. If one could change one's gender, transsexuals would be treated mentally, rather than physically. There would be no basis for sex reassignment surgery. We would simply have our "gender" changed to match our bodies.
Gender, we are told, is what is between our ears, sex is what is between our legs. In the case of a true or classic transsexual, the gender is truly different from the sex. In Sandeen's case, the gender and the sex are the same, and the issue is one of transgression. Sandeen is rebelling against what he really is, choosing to become, in effect, a "man in a dress." He wants the world to know he is a man, but he wants to force the world to call him a woman. It is a control issue, which of course, is typically male.
The simple fact is, Sandeen is lying, and he knows he is lying. He knows he is not really a woman, and that he never will be one. He doesn't really want to be one, but he wants to force society to accept him as one. The reality of his situation is ever with him. He whines, he complains, he accuses others of intolerance when they will not pander to his lies, but he knows he will never really change things to his warped concept of reality. And that makes him depressed.
Perhaps if he simply accepted reality, and stopped trying to deny it, he might feel better. He has been able to fraudulently obtain a court document that says he is female, but he is not female. He is now applying to change his birth certificate to reflect this fraud. He has tried to tell himself that this will make it all better. But he knows the truth. He will continue to be a man, and nothing will ever change that. Better that he accept his, and be happy being a "gender rebel," than trying to force people to pander to his demands. It simply is never going to happen. He may force clerks to put on a false smile, and say "Ma'am" to him, but he knows when his back is turned, they are snickering and saying, "Whoa, it's a dude..." And that is why he is so depressed.