There is a great deal to dislike. Primarily he is clearly from an affluent family and all his misery could be solved with a phone call.

What makes it seem like, from this piece anyway, that he is from an affluent family? (I don’t know the author/artist whatsoever.) Describe to me the phone call you think ought to take place.

"Hey mum, can I move back into your two-bedroom ranch house in North Carolina?"

"Oh honey, of course you can!"

Note that he did in fact move back in, so this conversation must have happened in some form.

That’s not particularly affluent.

He stole a $4k suit out of a store, for one thing.

The store will be fine.

How about he steals your suit next, you'll likely be fine as well.

Barney's new york is now closed, it was not fine.