Might be enough from you, but I still feel like I need to point out a strange assumption in your theory: That Octavia actually wanted to meet those bullies for a second time. I think it's more like they came to hang around the castle and Octavia sensed them and went to ask what they want again (though she obviously knew what they wanted, but I don't think it was really an arranged meeting as such). Who knows, but if someone tries to extort you, isn't it harder on the pride not to do anything about it?

Well, I do get your point partially. It wasn't probably that easy for her to let go of her background, even if these secret police dudes aren't exactly her former comrades.