As someone who likes to write fiction (publishing is another matter altogether), Bob's deconstruction of culture is frustrating because the man certainly can identify tropes the themes in storytelling, but has absolutely no clue as to how they work. He cannot, for the worthless life of his, actually put the damn thing back together. One reason for this is because Bob's narcissism and simplistic black-and-white worldview cripple his own understanding of the human psyche. As we have witnessed with The Last Jedi, he obsesses over "subversion of expectations" and believes that makes it a smart film. Fans are half-wits if they hate it as far as he's concerned.
The reason why the original trilogy as well as the Indiana Jones trilogy worked was because George Lucas wanted to recreate the excitement he felt when watching the old film serials of his youth. Thus he read Joseph Campbell's The Hero With a Thousand Faces and took inspiration from those serials and other films to (re)construct a film that many would agree is one of, if not THE defining film of the 20th century. Rian Johnson is postmodernist that believes that subverting the audience's expectations is somehow intelligent, which Bob agrees with because it fits with is ideology that the past must be torn down to make way for the Superior Future™.
No. There is a reason why works like the Iliad, Beowulf, and the works of Shakespeare are required reading in every university English program (and frankly, I would be surprised if Bob read any of them.) It's because they fulfilled a basic human need to look beyond this materialistic existence. Deconstruction and subversion are okay if the writer is skilled enough to put it back together. Alan Moore deconstructed and subverted the superhero genre with Miracleman and Watchmen, but was also able to reconstruct it with "Whatever Happened to the Man of Tomorrow," Supreme, and Tom Strong. Bob can't because he is too self-obsessed and motivated by instant gratification to look beyond the superficial.