Losing your freedom is a -100. That is, if you value freedom.
Depends on how long you're in jail for and if it's Club Fed, or a Super Max.
I'm sure there are tons of people that would be willing to risk a month or even a year in Club Fed for a chance at set for life money.
The calculation is different for everyone.
If in a game I can steal 10 points and at most get a 1 point penalty for getting caught, I'm much more likely to give it a shot than if I get a 10 or 20 point penalty for getting caught. Plus, if everyone else in the game is cheating and getting away with it, I'm much more likely to try it too.
The problem is if you make the penalties so severe and the application of the rules unequal, then you end up with chopping people's hands off for stealing.