I think most people would rather have a choice of routes, rather than a choice of plot events. The combination of these two led to a fractal division in outcomes that culminated mathematically at the exact moment that the update was delayed. Hundreds of possible conditions and events would be necessary to continue the plot even a little bit, which is almost certainly why he lost interest.
If I were picking this up again, I would create an in-world crisis that mirrors the circumstances of the creator, "something went out of control," and a partial reset in plot takes place. Some disaster happens at the school, which could be anything at all. Following that moment, the plot streamlines into a single path, and following that, every punishment, and every interaction involving more than one girl, has a small, finite number of permutations.