Your boy has Virgo rising with Mars in the 1st, squaring Pluto, opposing Uranus. I think he feels a lot of overwhelming burdens. He may feel irrationally responsible for impending doom?
I think he will need a lot of reassurance that he is not expected to right the ship, and make things better—things that are out of his control.
The Pluto in the 4th is about skeletons in the closet-family secrets—that he feels he needs to protect.
He may have a constant fear that things are imploding, and he needs to prevent it all from falling apart—but he cannot.
His Mars in the 1st, puts him at the forefront, and he feels personally responsible for so many things that are way over his head.
The Mars sextile to Jupiter in the 3rd gives him great insight and perception. He is wise beyond his years. And he picks up on everything—even things left unsaid.
That Jupiter flows into a Water Grand Trine—with Moon and Uranus. So he has great emotional force with his Cancer Moon. He feels things to the bone. He cares so deeply for family and close friends that he cannot always see things clearly. He is passionately loyal. A
nd it tears him up when he feels he has to take sides.
His Mother is represented by the Moon in Cancer in the grand trine. He feels much comfort and support from her and relies upon that supportive love. And yet Chiron quincunxes the Moon and Pluto opposed the Moon.
So Mom may not always see the subtle ways she might undermine her boys self confidence and self esteem. The Pluto opposition is out of sign and wide, but brought into focus because of the squares to Mars and the Asc in Virgo. It is possible that the child’s self critical nature is complicated by the intense need to not disappoint the mother figure because of his strong emotional attachment. He may wrongly assume that he is failing his family in some ways. That is an irrational fear and not anything you are doing.
The father figure seems to be a much more difficult equation here.
The Sun/Saturn in Leo in the 12th signifies Dad and the son’s identification with him. In his mind, they are one and the same, with the conjunction in the 12th.
The opposition to the Neptune in the 6th speaks of illness/weakness/instability. Perhaps there are drugs or alcohol or gluttony or overspending issues? [Jupiter in 2nd tsquare]
In short, the son may feel great disappointment in ones father figure, while at same time identifying closely with him and so feels sad or depressed in that he cannot escape the same fates?
The escape route seems to be in the Pluto 4th house reserves of inner strength. He needs to KNOW that he is his own person and he can overcome the weaknesses he perceives in those around him.
He needs to learn how to differentiate himself from his father figure while still allowing himself to love and respect him. Right now, I think he feels like everyone sees them as similar or same. It makes him feel awkward or uncomfortable socially and emotionally.
Mercury is the ruler of his natal chart. Mercury is in Leo conjunct Venus.
What are his talents/skills/creative abilities? These need to be evaluated and revealed so he can express them and have something to feel pride in.
His INDIVIDUAL strengths /talents need to be pin pointed for him. Separating from the intense identification with the family might be emotionally refreshing for him.
He needs to know that he has his own unique destiny and he will not necessarily always be in this emotional abyss that he feels is surrounding him.
I think the issues at school have to do with his own self critical feelings. When he can begin feeling better about himself his friendships will improve.
Having that emphasis upon the 12th house is difficult and it will not be easy to make lots of friends and feel like he fits in. So the goal might be to make a couple of close trustworthy friends and learn how to navigate the social scene without getting too caught up or upset.
I feel that his strength and deep reservoir of emotional resilience will get him through the toughest times. You might need to recognize how much he already knows and feels and recognizes about the difficulties surrounding his home life, and be more transparent, since he knows more than you all think he does?