i dont know if anyone will be able to answer this but is he still working on that blackmail thing from the school teacher job? Personally i think it was one of the hottest scenes in the game
If you're referring to Mr Bennett, you can pretty much give up on ever seeing that in the game. Even if he fully intends on continuing that storyline, the ultimatum he gives Sophia isn't due until playable day 17 at the earliest, and at the rate L&P's producing content, that could easily be around 5-6 years away. And that's being optimistic.
But, that's pretty much moot. L&P's already put in place a way for Sophia to just give Mr Bennett both middle fingers, with little effort on her part, so you can safely assume that Mr Bennett's path is as good as dead.
He was on shaky ground to begin with.