A couple of vague-ish ideas for the gender-bending stuff:
Have Joan and/or Charlie go to a bar where she used to go to as a dude and show her off to her guy friends from back then, maybe decide what she wears to it (with them being rowdier/leering more the skimpier it is). Either they don't know she was their old friend and just flirt with her, or they find out and mock/tease her about it to embarrass her more. Either take her there to establish her position as "your girl", or make her hook up with one of the dudes (turning the former manly man into a sexy housewife and humiliating her over it is a turn on).
With the Mayor, maybe some new political campaign stuff? Her now being forced to deal with how she's perceived differently as a hot chick, having to dress sexy/flirt for support?
Beasley and Davey: humiliation extravaganza! I LOVED Tina humiliating Davy when she was transformed. More of that stuff would be great, especially if Mrs Robbins gets involved. Amy and Catherine taking a role in humiliating Beasley and Davey's other former victims (Tracy, Kate, the police chief etc), deciding his punishments would be awesome.
I think I brought up Davey being made to wear skimpy outfits to school so people would leer at him so he'd be drowning in humiliation like Tina suggested, and yeah, that elevated her high on the Best Girl list in my eyes.
For tasks for the two I'm thinking:
Davey=
Skimpy schoolgirl outfit at school, maid/waitress at the hotel, a maid at the Ronald's Estate as punishment for misusing their teachings (Sarah would LOVE to have some to bully more than Lauren, the latter I see as being subtly cruel in a way that's extra degrading, maybe Roland lets loose his inner dirty old man, Angelica/Missy can take her out shopping in the maid dress/whatever else Davey is made to put on, in public), "girl night out" with mom and sister (skimpy dress up, getting her to strip and flirt, showing her off to people who ask where their son/brother is). Maybe have her join the cheer team (side note, is there any cheerleader stuff you'd be amiable to doing?).
Beasley=
The other teachers dress her up in the sluttiest teacher uniform they can find. Her students perv on her and they're happy to fan the flames. Maybe Catherine and Logan collaborate to dom her and stream it as porn? IDK.
Obviously, these are all just ideas, and I'm aware that you probably have a lot of other stuff to consider. I'm just hoping at least some of this gets added because TG like the above is my jam.