OK, still waiting for The Wasted Warrior

OK, still waiting for The Wasted Warrior. That's a film worth seeing. I would absolutely pay $10 to watch it.

The Dawn? Not so much, at least not as presented. Even in the 90s, it would probably have come off as either too offensive, or too sappy/preachy. It's very difficult to get the humour right so that you're targeting the unexpectedness, and not an entire community of people, some of whom will be in the audience. At the same time, you have to be true to the character, who almost certainly will not share that attitude, and is going to be horrified and disgusted at first. You have to portray that in a way that doesn't promote it.

I agree with the person in the film who said that it would be more interesting if the character retained his masculine attitude after the surgery, remaining true to himself (which is after all what transgender is about, and is also how we handle botched male circumcisions now instead of trying to make boys into girls) in his new body. You wouldn't see him magically become a good person, and you wouldn't see him in a dress, and he'd be taking male hormones, not female. You'd see him making use of his new body sexually, because he'd still have the same desire for sex. He wouldn't seek sex with men, because he's not gay, and that would violate mob rules anyway and those are important to him. But he'd have to be trying new things with his new body, maybe transgender women, or toys. There's a lot of comedic potential when he gains confidence in his new body, and realizes that making others uncomfortable with it can be useful and fun.

Done right, I think you could find an audience for it and make money. But it will never play the megaplexes in any form, because no matter how you slice it, you're going to alienate a significant chunk of the audience because you're either making fun of someone like themselves, or NOT making fun of someone they hate.