I agree with my True. Spare the rod and spoil the child.
At his age, my parents naturally saw to my needs. For any extras, as soon as I was big enough in size my Father provided me with a pushmower a gas can and two dollars to get me started. If I wanted something bad enough... I had to earn it. By the end of my very first summer "working", I paid him back for the mower, can, and the two dollars, as well as buying my own rake, and bags for fall leaves, and a shovel for winter.
In one years time I had my own bank account and the high point of my week was saturday mornings when I made my weekly trip to the bank. At times, my parents would step in and "gift" me financially for a few things I had really been working for, and I was grateful but never just assumed they would help. I had my chores at home, and was never given an allowance. The chores were looked upon as my cost of living.
I worked pretty much my whole life and work was always plentiful. I grew up in the country with a farm across the road, and another just through the woods behind my house. Our neighbors all worked and were happy to not have to worry about their yardwork getting done. It was done every time on time for the weekends and holidays weather permitting. Eventually I reached the point I could even carry them a couple weeks at a time if we did not hook up for payment.
I purchased my own TV, stereo, albums, reel to reel and reels, and 8-tracks (did I just date myself? LOL). I even purchased my own video system... a Columbia House system I think it was. Black and white, visuals sucked by today's standards, but back then it was really something. By the time I was his age my Parents bought my school clothes only because they did not fully approve of my choice of attire. By the time I hit HS... they gave me two new pairs of Levi's and two nice shirts for school and one suit as needed for dress occasions. I handled the rest on my own. I bought my own vehicles and bike... kept working as well as participating in extracurricular activities and sports in school, kept up my grades, and maintained my bank account.
Not bragging... just saying sis, that responsibility does not come naturally. I did not want to start working when I did. I wanted to keep playing with the other kids. Watching them having fun while I was doing work for their parents sucked, but once I got to realise what independence I had making my own money, and being able to buy what I wanted, (With parental guidance until I learned) I started to enjoy it. Not always the work, but the work was the means to an end. Soon I preferred work over play as I never got payed to play. I learned the value of a dollar, and the added responsibility at an early age really helped grow me up fast. I am still a kid at heart, and I hope I never lose that, but it is never to soon to shoulder responsibilities. Even a two YO can have responsibilities such as placing dirty clothes in the hamper to be washed, brushing their teeth and cleaning up before bed, etc. It is the responsibility itself... not necessarily the size of the responsibility. That will grow along with them. How would your Son feel if having worked hard for money he has set aside to buy something, it was stolen. Now it is gone. Nobody will just replace it free for him. He is out his money. Period... and in the process what he wanted to buy is now gone as well.
He seems to have alot to learn sis. Do your best to teach him. He will be old enough to start driving in a few years... and with that comes life and death decisions. He is by far not a lost cause. Knowing you as I do, he has a good foundation. Just rein him in and sit on him until he gets back on track. If he won't respect and obey the laws of the land or at home... fearing the penalty of breaking the laws of the land or home may serve just as well.