Anne is indeed a challenging character. So far, the MC has helped every girl out there to solve their problems and achieve their goals. But Anne's goal is to become the best whore in the world, and this game won't have that kind of NTR in which a love interest is getting pounded by other guys. So the result of her quest will be NOT making her the best whore in the world, and I find it kind of off-putting, since we'll be convincing her to not pursue her dream. I mean, I'm not particularly interested in making her the best whore in the world, but it's her dream after all, isn't it? So I'd feel kind of bad if I have to change her mind and make her 'save' herself just for my own amusement. And sure, we have already change Holly's and Myrtle's minds about some aspects like leaving the village or not accepting the woodcutter's death, but those were wrong choices by them and, deep inside, they didn't want to do that.
So I'm really curious to see how devs can pull it out in a wholesome way and convince us that Anne's wish is a wrong one.