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Gwen's damaged quirk: Have yandere mode turned on for a bit (Got it in ACT 2, trying to find side girls before going to the church to find the gem, like... when you sleep in the evening, her cutscene wil play.)

Chloe's quirks: Personality switch (Default - Slave for Original. Bimbo - Bimbo for the bimbo quirk, yeah, that's about it.)

Annie's lactating quirk: In act 2, finish all of  Annie's missions and find her in the barn house (The barnhouse has to be bought in Jessica's office.) at afternoon (Or maybe during one of her missions, It's been a while since I've done any of annie's missions.)

Jessica's quirks - Awaken Jessica and agree to have yourself call her auntie for the auntie quirk. Buy the dungeon and (during halloween) get spooked by Jessica and Gwen to get the adultress quirk (Must pick Jessica and fuck her.)
Luna's quirk: Finish all of Luna's mission, go for a walk with her and humilate via forcing her to wear farmer clothing (commoner clothes.)

Pixie's quirks: Buy a school clothes for dolls and school her in the college to get the schooled quirk. Finish all of both pixie and lyx's missions to have lyx give you the ability to enlarge Pixie, that way you can have 2 options: Fuck her in her medium sized body (I think.. like.. big doll size?) or fuck her in her large sized body (Basically, she's a short girl.)

Qarinah's quirk: Finish all of her missions and sleep until you get the beast dream. She will appear at the last message and confront the beast in your dream with her clones, to which she will forever scare away the beast from harassing your dreams, and give you the dreamgirl quirk.

There is a good chance I might be wrong on majority or all of them as it has been a while, but those are the tips to getting their quirks.