Honestly, it wouldn't surprise me if May were a lesbian - she's had a long track record of making sexualized comments towards both human and AI women in the comic, and she's been depicted as being disgusted by the idea of at least human male anatomy (Dale's, in particular).
I also wonder how an AI would react if their gender bit were flipped. Jeph's writings about AI gender were before his current knowledge of trans* issues (or even his current stance on AI civil rights), and I wouldn't be surprised if, if given the chance, Jeph would retcon that (he's certainly retconned a lot of other things about AI civil rights)... But, even back then, AIs had a distinctly separate gender identity versus presentation, which is what brought up that whole discussion. I do suspect that it's now seen as distinctly unethical for an AI's companion to flip that gender bit if the mechanic still exists, and I wouldn't be surprised if it's now actually immutable so even the AI can't change it (because a chassis change is possible). Although, then, there's genderfluidity that could come into play...