I can see that perspective. I just tend to think that Tom Hanks did a lot of good portraying a sympathetic gay guy, even though he's straight. If the portrayal and the story resonate with audiences in a positive way, and builds sympathy, I'd think that would be worth doing.
Maybe back in the day.
When Boys Don't Cry came out, it was made with a tiny budget. Brandon Teena never underwent medical transition. There wasn't a lot of precedent or social discourse for framing casting decisions. Hilary Swank, then unknown, was about as good a choice as any given the situation. That film, for many, was a form of exposure to transgender issues they had never had.
But eventually you end up with a pattern where even the sympathetic narratives are being told by cisgender people. Hilary Swank, Felicity Huffman, Eddie Redmayne, Jeffrey Tambor, Matt Bomer. Scarlett Johansen was going to play Dante Gill, but backed out due to backlash not only over this role, but over playing Motoko Kusanagi in Ghost in the Shell as well.
Swank, Huffman, and Tambor won notable awards for their portrayals. Tambor even acknowledged the representation issue in his acceptance speech. Redmayne was nominated for many awards for his role, though he didn't win. He, also, was fully aware of the issue of representation at the time of making the film. Bomer was also aware.
I sure as hell not claiming I am representative of Brandon Teena, Dante Gill, or Lili Elbe, nor that they are representative of me. But in order to take these roles, people like Redmayne and Huffman are drawing on the experiences of transgender people and creating a facsimile. While any one performance should be judged on its merits, when we keep repeating this pattern of cis people playing transgender characters, the end result is a depiction of transgender people which feels kinda superficial and off. It seems to increase in authenticity the more transgender people are actually involved in the creation process, but it still tends to feel a bit off.
And there are other issues besides. One of those issues is the transgender population is not hurting for competent story-tellers; we're just not as marketable as cisgender people. It's not that we can't talk; people have a really hard time listening. More cisgender people playing transgender roles is going to remedy that how? Due to our small numbers and historical (and in many cases current) disenfranchisement, there are always going to be challenges to being heard. The overwhelming majority of legislators, judiciaries, media personalities, pundits, and academics are going to be cisgender people. Even in the most egalitarian of scenarios, that's going to be the case due to numbers. Transgender voices are tiny quotes in articles, we are invited speakers, we are consultant credits, we are obscure indie art, we are tweets which are always interpreted as angry, but we aren't the main narrative in our own stories and experiences. Cis people talking for us... that's great in some scenarios when we don't have the opportunity to do ourselves, but it gets increasingly strange in those scenarios where we can meaningfully contribute to our own representation.
And while admittedly, this is a little petty, there is something odd about seeing a cisgender person getting awards and accolades for pretending to endure the suffering you experience. I count myself amongst the most privileged as far as transgender people go. When I say 'petty', I'm not talking about some deep, spiteful emotion. It's more of a "Well, that's a bit weird. Good for you, I guess?"
If Halle Berry had made this movie and it had done well for her? Great for her. She seems like a nice enough person. I don't think it would have broken her career. Redmayne, Tambor, and Bomer got through it fine, though maybe it would be different for a black woman or for an actress out of her peak fame. I don't know. But the primary beneficiary would have been her, those involved with the film, and audiences who enjoyed the performance. Nothing wrong with that. That's how it's supposed to work. It's just, I don't think transgender men or transgender people in general get much out of that, even if Berry's performance is sympathetic and compelling.
Representation of LGB people in film and television went (and to some extent is still going through) a very similar struggle.
And this is all only accounting for the sympathetic portrayals. It doesn't even touch on bs like
La Mante.