It seems interesting so far. I like the premise. However, considering that shear amount of women offered i am worried about keeping things straight. There is also a question on the analytics option(I am not accusing you of anything. Just curious on how the mechanics work).
Finally my last worry is the feeling of having bit off more than one can chew. The idea of a disgraced teacher given a second chance is a cool idea and rising above it, but then you throw the player not only having to be the headmaster AND running the hostess club. Just seems a bit much and I hope that all there is. Kind of a lot to throw at a player without much direction.
Other than that i will look on with anticipation.