Hello Derpsta,
Take note that the game is still in alpha, in very early stage of the development.
That said, you are right, I'm planning to develop a real Quest system that will tell the player what to do in the next update. I'm planning on adding a ingame phone system that will give you information about the quests, but also the different locations, the girls, the school in general, an online shop, etc.. It's a work in progress.
I will also investigate the bug you mentioned but normally, each time you put a can in the bin, you should receive money that will allow you to pay services from the girl in the back of the school.
Thanks for the feedback!