Part of this is because it was meant as a companion to Solipsistic which answered most of the 'world' questions - originally meeting the headmaster was going to involve a lot of exposition, but it kept getting bogged down in weird details... a lot of this is my own fault (Solipsistic was pretty convoluted

A quick summary is that the Headmaster is indeed a robot, controlled by Apollo who is an AI tending to humans in self-contained communities, in a 'competition' with other AI to try and raise the 'best' human by a convoluted series of metrics. These AI also try to interfere with each other's communities, such as providing Max the means to construct his remote control.
I had a rough idea of what graduation would be... largely robo-smut, but on the off chance I end up writing it I'll avoid going into more detail... australopith already had some great ideas about how Maya might factor into things. (Originally she was going to be brought back at the end, but I settled on the Megan route).
Speaking of Solipsistic, I finally finished the epilogue that had also been sitting around for years and years. It's up on Fembotwiki