Just got the Villain Tag. Currently in Fort Joy. Got level 2 on the ship (attacking door guard on the way to Windego with the door open), skipped straight to the top of the ship, shot the child to skip the dialogue and to not have to save anyone. On Fort Joy, I deceived the Unnis into giving me her money (cannot do this as a human/undead human without Fane's mask), killed the turtles, assisted Ifan in dispatching with the two thugs, then assisted in freeing the locked elf by convincing the Lizard to give me the oranges, then ratting him out. Then I stole the Sparkler card, used it in a game with the three thugs on the tower area, then killed them. This made me hit level 3 and obtain the Villain tag immediately. I doubt it's relevant, but I skipped the dialogue with Atusa, Dallis and Alexander by climbing up on a ladder to the side of them.
If this doesn't work every time, then this system is probably random chance.