If stealing cargo was your thing, and there was only a 10% chance that you would succeed at doing it, this would be difficult (9 out of 10 attempts would result in failure). But if stealing cargo was very easy to do, but then 90% of the time you got caught afterwards and had to 'sit out' the game for an hour, you wouldn't have very much fun doing it. The point is that on the one hand, we can make succeeding at a criminal action very difficult. We can make the odds of success low through the way we design all the defenses against that action (security forces, self-defense, escorts, etc.) And then we can attempt to hurt the player after the fact for having done those actions. If we do the first, if we make criminality really difficult, we've succeeded in making this choice into a 'hard mode' for the game - one that many will attempt, but few will succeed at. If we try to do the second method, by making failure suck so bad that it hurts the player, namely by forcing them not to play the game, then you have simply failed to design a fun system, regardless of difficulty. Failing at criminality should not be odious to the person who failed. Like any other attempt in a video game, it should simply result in the player who failed to have to start over again at some point in the past. That is, they should, just like any other failure, have their progress reset so that they have to keep practicing until they get better. At no point should we ever consider trying to make the player themselves feel bad for choosing a particular kind of gameplay that we want in the game. That is, we are not "punishing" the player, we are simply forcing a progress reset on their character, just like fail mode for any other style of gameplay. When it comes to prison, this is really dicey, because forced downtime, or "sitting out", tends to be squarely aimed at hurting the player, not merely resetting their progress. Now, that doesn't mean that I don't think prison has any place in the game, it is extremely immersive for one, and I really like that. But we have to be very careful about what we mean when we say we are "punishing" someone for their actions. We can make criminal gameplay loops difficult - before prison. We can make the chances of success lower by giving the defenders advantages that help them fend off pirates in the first place. We can make it HARD for pirates to succeed as pirates. We can do that without making the game suck for them when they fail.