I'm going to say that he wouldn't. At least, not anymore.
I don't think Oda is transphobic at this point, but he did have some highly questionable portrayals with the Okama and Sanji's behavior towards them. Plus, Sanji had to have fought 99 of the Newkama Marital Artists to get his ship so...yeah.
I do think Oda has changed though, with Okiku being the prime example of a positive change. And considering Sanji correctly identifies her as a woman, having rescued her along with the rest of the ladies when Kaido attacked Oden's castle, I think he's changed to reflect Oda's current thoughts, but now in a more positive manner.