Playing a strong character, I've found out you can beat Bailey rather easy, combined with the Excellent English and Excellent science traits. If your pain meter is around 70% during combat with him, you can always choose the Apologize option just to beat on him some more, before he's defeated.
Problem is, during the next encounter, this asshole decides to bring a thug as backup. Now it's even harder, but if you pay Bailey then, during the next encounter he will not bring the thug along, it resets.
I know that his rent day is avoidable, but I REALLY wanna raise that rebelliousness up - stoke the fires of a revolt even more and hopefully see Bailey dragged from his office by an angry mob of orphans one day.