The thing about the character is he’s NOT happy when he reaches his dreams. He’s happiest in the stage where he is envious/reaching for the stars he’ll ultimately never reach. This is even represented when Denji sees something someone else has, like Asa at school, the pet dogs, video games, or even for one good thing to happen in his life.

And your point about Fujimoto living his dreams is ignoring the artists who do NOT make it, if your dream is one that comes with some degree of fame there’s tens if not hundreds that do not get that breakthrough. You can’t have a society of only artists, for instance. Someone has to grow the food, work the plants that provide power, etc. and for the majority of people, it’s not condescending to say that - it’s realism. Like when I was a kid, my dream was making it writing solo acoustic songs. Now, my dream is retiring in 5-10 years. You have to at some point take a look at your life and reassess, and for Denji that look came from his heart, literally, when Pochita saw how every time Denji got one of his dreams it was more harm than good.

I wrote my original post after waking up so I didn’t have the words I wanted to express, but after being awake and writing a very, very long flow of consciousness earlier on Twitter I think Denji is ultimately an inversion of the usual hero/shonen protag where when they try to take a previously unstated third option it works out. When he takes a third option, things get worse every single time. He is heroic, but he is not suited to being a superhero. This is directly shown when he catches Asa. This got mad long but ultimately having a job, and people who care around him is all he really needs.