Serious Crimes and Punishment

The "Serious Crimes" option is available at Chuunin/Lower Outlaw. Serious crimes allow you to perform a crime in which you could go to jail or gains vast amounts of money.

When engaging in serious crimes, it will cost you 50 chakra and 50 stamina. You will lose 20-100 reputation in the village.

On the other hand, you could gain hundreds of ryo in one sweep. If your speed and willpower are too low, you may be caught and placed in jail for 30 minutes. In jail, you can not engage in any action EXCEPT training general strengths.

Robbing Users(OUTLAW ONLY!)

Believe it or not robbing someone does not solely rely on "luck" there are actual things that come into effect when robbing someone. To better understand this I have put together a "formula" which pretty much means your stats get added up and they go against the stats of your opponent.

The formula for succesfully robbing another player.

Outlaw Points = Outlaw[taijutsu_strength] + Outlaw['ninjutsu_strength'] + Outlaw['genjutsu_strength'] + Outlaw['weapon_strength'] + Outlaw['speed'] + Outlaw[taijutsu_defence] + Outlaw['ninjutsu_defence'] + Outlaw['genjutsu_defence'] + Outlaw['weapon_defence'] + Outlaw['intelligence'] + Outlaw['strength'] + Outlaw['willpower']

User Points = User [taijutsu_strength] + User ['ninjutsu_strength'] + User ['genjutsu_strength'] + User ['weapon_strength'] + User ['speed'] + User [taijutsu_defence] + User ['ninjutsu_defence'] + User ['genjutsu_defence'] + User ['weapon_defence'] + User ['intelligence'] + User ['strength'] + User ['willpower']

If Outlaw Points are over User Points x 2, then the robbery is successful.
Hopefully this will clear up the confusion of whether or not you CAN or CANNOT rob another person.