The thing is, a lot of those things seem at best loosely related. There's no flow between them, and at times they seem mutually exclusive. I think Rainces just forgot what his plans were at times, or was more concerned with creating new content where something minimal happened, but in sum it never really lead anywhere, or did so very slowly. The totality of everything that happened should have resulted in more happening, but it is like many of those events occurred in parallel universes. Failing student Lucy even feels like a different character than party-girl Lucy. The bad student storyline probably should have gone to Jenny. Or Bobby's approach to helping Lucy with her grades should have gone the route of him offering to help her cheat in exchange for... stuff. He could grind some online courses on hacking to change her grades or steal answers, or seduce some nerdy milf at the school, or something like that. Maybe he even takes over paying Lucy's tuition after Anna cannot, but with certain conditions. I think thematically, those would have been more on target with Lucy's other events and overall personality. Lucy strikes me as not terribly interested in either school or a typical job. Those are means to an end, in this case just paying bills, but also buying nice stuff and allowing the lifestyle she wants. Bobby's opportunity there isn't necessarily to help her become a better student. It should be to offer her an "easier" alternative than studying hard and getting a real job. He'll take care of her, if she takes care of him.
I like the fact that you think about the game and the characters. Most people just want to see Bob having sex or raping them, regardless of the context.
It's clear that Rainces started the game without a clear idea of what would happen. Ideally, he would have planned out each character's entire arc and established personalities, individualities, etc.
But Lisa's arc in the last update, while I found it a bit too heavy for my taste, was quite cohesive. It's basically Bob psychologically breaking Lisa to the point where he rapes her, which would have led to a Game Over at earlier points, but instead, the game continues.
"The bad student storyline probably should have gone to Jenny. Or Bobby's approach to helping Lucy with her grades should have gone the route of him offering to help her cheat in exchange for... stuff. He could grind some online courses on hacking to change her grades or steal answers, or seduce some nerdy milf at the school, or something like that."
Yes, this plot could fit Jenny too. but Jenny already had that arc where she works at a strip club, which is more surprising than if it had been one of the older sisters. But regarding this plot, remember that Bob promised Lucy that he would steal the tests for her. However, I don't think Rainces managed to finish this plot. Bob pretended to help Lucy so he could just slap her ass haha or comfort her by caressing her body.
Lucy isn't interested in school, but like most girls who live with their parents, she needs to go to school and study. Her mother gives her money and lets her go out at night, but if she does poorly in school, her mother certainly won't give her any more money or let her go out anymore. It's not that out of character. Supposedly, everyone studies, even though we don't see Jenny or Lisa studying, or even Bob going to school. There are many holes in the game in this regard.
