Christ.
I think he is as you said, at a crossroads to where he could become an arrogant shit or remain humble. He says he’s an old school gamer so I have high hopes for the latter, he just really needs to educate himself more on the game and get far more experience, because while he may not mean to, he is doing similar to bloodyyautja69 in giving poor advice to others. At least he’s nice about it and doesn’t put them down. I think as long as he listens to people like us who’ve been around the lifetime of the game and continues to stay humble he will do very fine.
I almost want you to analyze my FT play, but I’m too afraid to get my feelings hurt lol. Might be helpful though, I’m always willing to learn.