But not fond enough of him to not cuck him
Ik it was a joke (a good one too), but that really depends how it's gonna be written.
The main girl for example I can see a lot of blackmail and tomfoolery going on in the beginning phases, middle phases probably some embarrassment in the sense of "I don't want him to find out im doing stuff like this" and of "not being worthy" because she's been "sullied" so to speak. Naive ideas of purity and perception and whatnot, that will maintain the relationship to whoever is using her for sex, and then the end phases will be acceptance of her behaviors, with either her committing to another dude (antagonist-specific end phases and bad ends) or becoming a full nympho. Alternatively ofc the "breaking free of it all" and getting together with the MC after all ("good" or "bittersweet" kind of ending).
The landlady/mom-type figure I can imagine just doesn't realize that their relationship is a possibility. There is various ways how this can be played, tho Im no expert since Im not that much into the mom or stepmom types.
The teacher/superior girl I will be curious about, but she did not have a relation with him from the get go so there is that.
And the blacksmith I think he already got some action with, so I wonder if she is gonna be a possibility for him to turn to when he gets cucked. Like eventually becoming happy or at least settled and satisfied with her.