No, he won't ever reach an acceptable version of womanhood.
There are two reasons for this.
The first reason is very simple. Womanhood means being female. There is nothing in the world that can make Dylan female, so he will never be seen as a woman by those of us who believe a woman is a female person. I might as well moan that I could get a tail surgically attached to my backside and only speak in miaows and it still wouldn't be enough to make people see me as a cat. Well, no. Obviously not. Because I wouldn't be a cat.
The second reason is that, even if you agreed that womanhood is more of an identity, or a set of behaviours, or something socially constructed, the version of womanhood that Dylan has chosen to portray is offensive to most women. It depicts us as vapid, simpering idiots. Not serious businesswomen, politicians or athletes. There is nothing about the image Dylan chooses to project which is flattering to or indeed truthful about most women.
Dylan could have said, "I am transgender. I identify as a woman. I may not have female body parts but I feel very deeply that I am supposed to be a woman. I love women. Women are amazing. Oh hey, look at what Ruth Bader Ginsberg achieved in her life! Look at what Simone Biles has just achieved in Antwerp. Today I'm going to share some of my favourite books by female authors including JK Rowling, Chimamanda Ngozi Adichie, Isabel Allende and Arundhati Roy. Who are your favourite female authors?"
When approached about doing a collaboration with Tampax, he could have said, "You know, I think you should ask someone who menstruates to be the face of your brand. It feels like appropriation for me to do this."
Or he could have said, "Hell yes, I'd love to do this collaboration with you but it needs to be centred around women and girls who menstruate. Could we maybe do a publicity campaign which also does some good, such as raising awareness of period poverty, or the fact that in some parts of the world women and girls are still confined to menstrual huts?"
He still wouldn't be the right face of that brand but he could have done that collaboration in a way that was much less weird and creepy. Instead his behaviour around it and his apparent obsession with tampons just screams the glaring obvious but we are supposed to not say anything and not complain because that would be transphobic.
For me, Dylan will never be an "acceptable woman" for the first reason: because he's not female. But I would accept him as a trans woman and use his preferred pronouns and be respectful of his identity if he projected a version of womanhood I could actually get on board with.