Finally, a modern game. The main pitch is great. The pictures chosen are lovely, the writing does leave something to be desired but is in general adequate. Having Cain being a walkthrough is very good. I especially like how pictures are often placed to the side, with text on the other side. Adding more gifs would improve that.
There is one point of criticism, since this isn't so much a game (you can't lose!) as much as it is a visual novel, it makes no sense to have a billion empty rooms. Reduce the number of places the character can visit to the absolute minimum and railroad more. You do not need all these classrooms. There is nothing in midtown except for the comic store, pull it out. Don't crowd out the menu with places that have no functionality.
In general, I think a less sandboxy style, like college daze would serve this concept much better.
