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He should gain a half-Feline form. Sort of like a Beastkin or sort of like a Fortnite’s Meowscles type.

Also, Pickpocketing, Sleight of hands, and lock-picking. Very useful if necessary

He could bring the guitar with him when travels, possibly hide some of his weapons in it. This could be a small reference to El Mariachi trilogy. The protagonist is also played by Antonio Banderas. Also he should learn dagger/knife skills. He could use it as a secondary weapon to either distract or temporarily harm opponents.

I hope you could an Homage to “Yojimbo” by Akira Kurosawa as one of his exploits.

How many grades did John skip? If not, when will he do it?

Can you also write and show scenes of his schooling, making friends/connections as well? It would help make the MC interesting. Also I would like to see John teaching Sheldon moments too.

I agree, but also someone Sheldon to begrudgingly learned to be humble from.

Well, this would be a good chance for your MC to be a great influence to his siblings in order to direct them into a better focus, especially Missy and Georgie.

So far, it is alright, it has a lot of potential to going to different directions. I feel like it needs a bit more dialogue, descriptions, and little more world building. Maybe throw in a few curveballs and some problems the MC needs to deal with. Make the character feel more real, have him some flaws, make him face challenges. It would make the MC varied and nuance with his personality and traits. I wish you the very best on writing this!

Make sure to put on year and dates, it would make it easier to keep track of time and story.