Gameplay Idea: When upgrading a device and how they can't do certain things unless upgraded (Glamour Slam's stripping & specials or Bordello's private & exhibition, etc). You should be able to make them do those things anyway but, with a chance that they brake free from the device's control and escape, then have to capture them again.
Example: Batgirl has the basic level device that can dance at the Slam but if you make her go to the next parts without upgrading (because you need the money or something), she has a chance to brake free from the device. You get a notification the next night of the escape so you can go capture her again. The more elaborate the action, the higher chance they break free from the inadequate device.
I know that's not the point of the game but it could add more layers to upgrading devices and the game. Also could have some unique dialogue when capturing them again. It's probably a long way until it even gets to that point but just a thought.