Not really. That quest allows you to remove Ruth's block on you punishing. If you enjoy the content, you want to play that one out as long as you can, and even after he clears the path, don't break Ruth until you have all the other girls as far as they can go.
Copying my comment below, I think you have to progress the science teacher's quest until you unlock the final headmaster journal entry before Jimmy will clear the way. You need to read that before you visit the woods.
