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One of the NPCs I wrote for the Adventurer's Guide, the leader of the redeemed Maidens, is a trans woman. So, yes. ^_^
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Cool, I look forward to checking it out. Though... I wonder if I could pester you to at least offer some speculation about whether or not they would pre-redemption? I mean there's really no wrong answer. If not, they are the bad guys after all, and if so, then Even Evil Has Standards. Obviously, a GM could rule either way for their particular game - and I for one tend to treat canon, especially in RPGs, as more of a suggestion than immutable rules, anyway. So this is entirely just to sate my curiosity.
Well, it really comes down to the question: is she pretty? Because that's the only real reason Ileosa made the Gray Maidens a woman-only group; she hates other pretty women and so scarring their faces and indoctrinating them to be slavishly loyal to them warmed the cockles of her black heart. If said AMAB person still makes for a pretty girl then it's entirely possible that Ileosa will have them "volunteered" for the Gray Maidens.
Now, if you're talking about afterwards? Well, Erinyes Company (the LE branch in Cheliax) probably doesn't care so long as you're willing to devote yourself to their ethos, follow all their rules, and can hold your own in a fight. And the Scarlet Rose (the NG ones in Korvosa) doesn't actually recruit new Gray Maidens, it's more a support group for the old ones to help them get over their programming and reintegrate with society. That said, the "face" of the Scarlet Rose is actually a MtF transexual (via a magic belt), so at the very least said AMAB Gray Maiden wouldn't be treated any differently if they joined up.
How other Gray Maiden factions (like the ones who camped out in the Lady's Light in the Shattered Star AP) would react would be up to the individuals who lead them.