Somehow I think gabby viola might be a path that's being set up. and honestly, pepper seems the most pragmatic for like... She'll compromise herself and justify it after, living with the rationalizations until they stop being rationalizations and just become acceptance.
It would be so fucking hot if Gabby & Viola 3some happened, but I'm not sure if Gabby would be up for it tbh. On Gabby's romance route, I could see MC coming back to his apartment after a good fuck with our chocolate princess and letting maid Viola suck her pussy juices off (still don't know anything about Viola, so this is pure guesswork obviously; oh god, or imagine if MC didn't tell her they did anal and she sucked her ass off instead
). So, Viola might get second-hand Gabby. But, as far as an actual threesome, we might only be able to get it on the corruption route... which might be an interesting and confusing affair, for both girls, but especially for Viola. On the one hand, Viola finally getting her Gabby on a platter... but on the other, if Gabby's not fully into it and is just doing it because of money... she might be disappointed and guilty during/afterwards... the infamous "post-nut clarity" in action.
And, yeah, I guess I kinda see your point with Pepper. She might also sort of be like a spitfire Nicki, where she aggressively vocalizes her displeasure, yet still goes along with it anyways even though she doesn't really want to. I mean, I guess to an extent they're all like that, or else we wouldn't have a corruption/dark route. Nicki & Brit stand out in that regard to me, though; they seem the most likely to confuse what others want from them with what they want themselves, if that makes sense. Mason too maybe once we find out more about him. The rest of the girls may also be meek in the face of MC's power he lords over them (in 2 routes anyways), but I think they know what they actually want in the end for the most part.