Cindy is certainly chaotic neutral, bordering chaotic evil. I have plans for some endings and paths that would involve her alignment changing along with other characters.Love it. I was wondering: Cindy's character progress seems ripe to take a turn towards an evil alignment, rp wise, but she also works well as a neutral "force of nature" type. Are you going in either direction, or even considering making it optional how her motives are perceived? For example, it's easy to make her cruel to cucks when pushing the MC towards netori, or simply adventure driven, even giving out general advice (as she does with the professor's suitor, in the tone of "get the hints, this doesn't have to be hell for you, man up or look elsewhere"), not particularly concerned with their well being, but also not sadistic.
But those alternate paths will need to wait until I've done more with a singular route. As adding branching paths creates a massive amount of work. Once I get a good base I can go back and create expanded alternate paths.