Child and punishment, would a time-out be an effective punishment for showing the seriousness for these kinds of misbehavior?

Child and punishment, which of these situations would a time-out really hone in the severity to a child 10 and below?
With all the recent talk the past few weeks about crime and punishment, child and punishment, I wonder just what is severe enough to go further than just 15 to 30min time-out in the naughty chair? If any of the following situations happened which do you think a time-out would do, and that the child would truly know the magnitude of such an action?

• Keying cars paint job.
• Tossing items off the over pass into traffic.
• Hunting down neighborhood cats with a pellet gun theirs or some one else’s.
• Tee peeing a house.
• Chronic sucker punching of siblings.
• Playing with fire in the house.
• Trying to get their sibling to jump off the roof or climb to the top of a tall tree.
• Trespassing on private property.
• Spitting on teachers, or slapping them.

Which do you believe a time-out or grounding will work for when used once? If used once won’t curb the activity how many time-outs and for how long will it take to get the point across? If you take everything that there is to take, toys, cell phones, TV, etc and it still doesn’t curb the activities, what do you get to work then, shoot for therapy? Get the child on some mood altering drugs, or what?