Love everything I'm seeing here... and the 'issue' of having to write four different endings per character doesn't exist, as the game is already being built around that.
Essentially every character story is either a normal story (Twilight working herself to exhaustion in preparation of a big exam) or a bimbo story(Twilight enjoying her new body and attitude too much to actually study as she should be maybe (we haven't decided on this one yet)), and each of those stories has a good/bad end.