1.: You can attempt to do illegal things right from the start. What you can try and what you can’t depends on your larceny skill. This can be raised by committing crimes successfully (there is a textual clue).
– At first you can only go for shoplifting (Intelligence).
– Once you reach lvl 1 you can attempt purse snatching (Fitness), pickpocketing(Intelligence) or running cons (Charm)
– Once you reach lvl 2 you can try breaking into cars (Fitness), running more compley cons (Charm) or blackmailing (Intelligence).
2.: Your chance of success is determined by your skill level with the associated skill (see above) as well as your Larceny skill. Successful attempts will earn you money and/or item rewards.
3.: Dealing drugs is a special kind of crime activity. It is covered under ‘Drugs’.
4.: Getting caught by someone while committing a crime is not the end of the world. You have an option to avoid getting the law involved by going along with the demands of the person who caught you.
5.: Getting caught by the police is a more serious matter. You can get caught while doing any of the crime above as well as for public nudity, cheating at the casino and for refusing to work with Mrs. Spencer on her forced path.
6.: Once you get arrested you are slapped with a fine. How much you need to pay depends on your criminal record as well as on the type of crime committed. Paying the fine will let you go free but it won’t clear your record!
7.: If you can’t or won’t pay your fine you can attempt to bribe the officer into letting you go either with a lower amount of money or with sex. Your success depends on the money offered or your Charm skill as well as the fine you are trying to avoid. An unsuccessful amount means extra jail time.