Jail's in the city now? Sweet, I've been wanting to visit prisoners for a while. That should be fun :)
What if there is an actual visit area, or a place where people can post bail? And while the visitor is in the booth opposite the prisoner, they (and only they) can see the chat from the prisoner they are visiting? That would be pretty neat, yo. Could be fun for prisoners to make their appeal for bail to their fellow mobsters, or even their mob boss. I'd be so down for that!