Yes. When you are this far along, at least. We’re at the point where all the groundwork has been set up, and famous people who are part of the cause can come out in support without jeopardizing their fame.
Jenner came out because, to some degree, it is acceptable to come out. She would not be overwhelmingly seen as a laughing stock or a carnival attraction. She could not have done so with those who came before her. Heck, without the groundwork, she might not have known she was trans and not delusional, nor would doctors have allowed her to be treated.
If it were just about money, then making a freak show like Honey Boo Boo would have been the way to pull it off. No, it’s about acceptance. We’re at the home stretch in the push.
Money plays a part, but only because acceptance is so far along.
Assuming the typical situation as I understand it, Caitlin won those medals, as she was female the entire time, and Caitlin is her female name. There is, however, some talk of gender fluidity, which may complicate cases.
As for your other question, my understanding is that dead naming is an issue not because it’s the wrong name, but because it refers to the wrong gender identity. It’s an issue of being misgendered. So, assuming “change back” means adopting their original gender identity, and assuming they don’t adopt the same name as they had before, I would think the worst name would be the one that is the wrong gender.
The other name would seem to be the same as calling my dad Jimmy when he goes by James now–except it could also carry with it an implication of the rejection of transsexuality in general, which would be more offensive. But at least the gender would be correct.
Of course, Una may come in and completely disagree with me. I simply try to learn what I can.