Okay, only screenshot I'm going to post until I've got real art in there. Honest!
Right now I've got all the basic dumb engine stuff down (with just a couple of inventory bits needing to be sorted out). That's the part I actually know how to do! Next up: figuring out how to actually create stories.
I've got a fairly simple structure for it worked out: first, pick a story premise (e.g. "Izumi runs for class president"). Set it up with an initial event explaining what the first set of obstacles are (e.g. "convince people to vote for you"). Then, generate obstacles using available characters (e.g. give study notes to Ken to get his vote), with the obstacle depth (e.g. Hazuki won't vote for you unless Ken is) being determined by the premise, since some should be more linear than others. Finally, put an end condition early on in that tree (e.g. tell the teacher you're finished campaigning), and when it's reached, give a premise-specific ending based off how many obstacles you've completed (e.g. "Izumi becomes president!"/"Izumi tried, but didn't get elected."/"Izumi even care!").
Once all that works with that very specific scenario, I'll figure out how to actually generate obstacles generically. I can probably get away with premises being less random. But I'll worry about that later.
Okay. I can
totally do this.