I plan to have him do extra chores around the house/yard to work off the cost of replacing the window. What do you think? Any suggestions would be appreciated.
The natural consequences of his breaking the window are for him to replace it so your discipline is most appropriate and fair. It might help your relationship if you told him you understand now why he got so angry with you. Try to let him assume more responsibilities like his self-initiated flyer delivery, he's trying to grow up and separate from you, get his own adolescent identity. Help him out on occasion.