Or you know, you fail a pickpocket attempt, but you can just bribe the guard and then speak with your victim like nothing just happened... Similar problems occur with vampirism: My character is a female dunmer who wears the ancient DB cowl all the time (so she's masked and all), but when she's blood starved EVERYONE can see it... And this leads to the second problem, as she can feed then go back to the same city without anyone recognizing her...