B.M.
Hi Stephanie,
This must be very frustrating for you. But I think you may have some things you can start to do today that will have some immediate effects with your son.
You've asked a couple questions, so I'll try to give you my take......
At 4, your youngest is old enough to respect someones room. Why does the responsibility all go to your oldest son? that is absolutely not fair to EITHER of your kids, and not only will it make your older son get worse and worse it will breed a sense of entitlement in your youngest. Your oldest son should be 'nicer' but your other kids should respect his boundaries. It sounds like he has been jealous from the start and he is only close with the middle because they have a common enemy - the youngest!!!!!!
It doesn't sound like your son has been taught appropriate ways to handle his anger (first at being replaced by younger siblings, then by being punished instead of disciplined, now by being disrespected by his family). So I would start there.
If he is interested in skateboarding he should do it MORE, not have the one thing that he loves get taken away because he can't do anything right when it seems like his world doesn't care anything about him. Skateboarding is a sport that takes discipline and practice. Can you formalize it and get him a 'coach' or older mentor who can spend time with him?
I would also find out if there are other activities he can be involved in - tae kwon do does WONDERS for self-esteem and discipline. Additionally swimming, church youth groups, basketball etc would do him a world of good.
As far as the school work - Does he have structured homework time? I bet his teacher would email you what his assignments are each week. Or at LEAST she should be working with him on making a LIST of what he needs to turn in and when its due. Then he sits down every night at the same time and works through his schoolwork.
Instead of punishing him for bad grades - TEACH him how to get the grades he is capable of. No one LIKES to do something they are bad at. But he won't like it until he feels confident. He needs study habits, organizational skills, and encouragement rather than punished when he does something wrong or gets a bad grade.
Please please please please please try to see this from your eldest SON'S point of view and not anyone elses. If you don't let him know that you respect and love him and teach him the skills to succeed he will be a mess when he is a teenager.
Oh - I'm adding: You can't MAKE your kids be closer. They didn't pick each other. What you can do is make sure they EACH have their own lives and interests. You can foster a family environment of respect and encouragement. They have to see each other as teammates rather than competition.
Good Luck.