Hamilton is an interesting one.
On the one hand, it's kind of uncomfortable watching black men play white men who undoubtably benefitted directly or indirectly from the slave economy. In reality we know no actual black man would have the opportunity to get anywhere near their social, political or economic level.
On the other, it's great to have a huge hit show with great roles for black actors. There is undeniable power in seeing an almost entirely black cast play people of social, political or economic power, and it recontextualises that while these people were of the social elite, their success was not a done deal and they were also politically at least outsiders trying to change an established order.
Applying this to SIX - I think an all male cast could work, with an interesting tension between the social construction of male power and agency and the constraints these women lived under. However but given that the underlying power difference runs the other way, I'm not sure it would be possible to escape a sense of watching men punching down / Marie Antoinette playing milkmaid.
But that is casting a male cast for the deliberate effect. Like Hamilton, where retelling the story with a black cast is supposed to change it and raise new questions and perspectives, the point of casting men as the queens would be because they are not women. We would be supposed to notice and talk about that.
What I think does not work, and cannot work, is casting one male trans "woman" under the conceit that this male person is an actual woman and therefore someone that could in another time have been Anne Boleyn. We are not supposed to notice this crucial difference between him and Anne, or consider the underlying power differences, or how Dylan's "womanhood" would have played out in Tudor Britain vs that of actual women. All the perspectives that might make a male actor an interesting interpretation for the role are vorboten, unsayable.
Which is why it's not going to work. Because it's motivated by ego not the needs of the play.