I'm fairly certain that the game is still in the stages where you need to start a new game each time, hopefully this will be fixed eventually.
I went the route where I beat up the boyfriend, put Alchemy in the dungeon, and have gotten the footjob with no socks from Elyon, I'm teaching at the high school, but have not found a way yet to make certain that Will's dad gets outed as a non-reformed gambler (probably end of story atm), I've also gotten 2 scenes with Teranee, and then when I go to teach it kicks me back to the shop, (again, I'm guessing end of content). Cedric really needs to invest in some mind control magic, sure it probably won't work on the princess, or the guardians, but it would really help in taking care of those annoying normals.
Granted by the point the student blackmails you money should not be an issue.
For those who can't or don't want to use the cheat menu, you can also gamble in the tavern for 10, 20 or 30 gold. Although if the author reads this, he might want to put a bit of instructions in about the game, I was able to win fairly consistantly by scum saving, but I hate doing it like that.
Anyway, fun game so far.