I personally would not like to see a jail represented in The Sims, but I would be okay with Sims being caught / imprisoned for crimes and disappearing (the same as when at work or school) during which time they are unplayable. That would punish the player for having gambled and lost with committing the crime, and give some amount of stakes (lost time in the game, etc.). Meanwhile, the 'visiting in prison' mechanism could still be active by sending a different Sim to visit (disappear the same as at work or school). This would be a much simpler implementation that I think could actually happen, without requiring a whole pack. Also think it would be good to limit this to happening just to Sims who are in the criminal career, because otherwise non-player Sims might be constantly disappearing to prison and it might affect Sims who would otherwise never commit crimes in terms of ongoing neighborhood story action.
