Bob has a religious blind faith in the power of Experts. Remember when he wanted to get rid of the Democratic primary and just have some unspecified elite experts appoint a candidate? It's because everything bad stems from stupidity, to which Experts are immune, just put every decision in their hands and everything will be fine. Bob doesn't have the slightest notion that some problems are just really hard and even the most Expert-y of Experts can't solve them yet. Bob has even less idea that some problems are literally impossible and will not be solved ever. This is an idiot who thinks that we are on the verge of rewriting the laws of physics. Bob doesn't want to think about the fact that experts can be corrupt and work in their own best interests rather than his. Bob very definitely doesn't want to think about the possibility that the process for certifying Experts has itself become corrupt and will give out unearned credentials to people of the "correct" gender and skin color and political beliefs (see: fat black idiot Stacey Abrams graduating Harvard). For Bob to contemplate these possibilities is for Bob to contemplate a life without higher guidance, and anyone whose ever seen a religious True Believer contemplate the thought that God doesn't exist knows how upsetting that can be.
I think he gets read into too deeply to be honest. I don't think he puts (or is capable of putting) as much thought into his silly posts as the people who micro-analyze him.
I doubt he's ever read a book on any of the subjects longer than a video-game instruction manual, and most of his ideas about "robots" or whatever come from TV and comics; rather than any actual book on the subject such as Asimov.
(My understanding is that things such as "robots" and "people" are dichotomic to begin with; basically there are certain "tasks", usually ones which are easily repeated which can be "automated" by robots, however the "tasks" in question are only very small part of the overall "package" to begin with, and only exist that way in pure abstraction or speculation, as opposed to any real actual "job, task, and so forth".
So the whole thing is just based on a handful of simplistic, unoriginal axioms backed up by circular reasoning (not to mention the simple economic reality that any "jobs" or "tasks" which were automated would create "new jobs"; which has been the case throughout history - e.x. the printing press created new jobs for printers and print machinists; the automobile created jobs for auto designers and manufacturers; the personal computer created new jobs for computers and web designers).
So no, I don't see anything remotely "contemporary or cutting-edge" about Bob's "job" to begin with; social media "Jobs" are dime-a-dozen and haven't been "contemporary" since the earily 2000s; most of Bob's commentary is unoriginal, ADHD nonsense written at something like a 6th grade reading level which could be easily automated or replaced.
Bob basically just "shoots fish in a barrel"; by imagining one of the stereotypically stupid clods who bullied him HS (like "Moe" from Calvin and Hobbes), when a lot of the actual "meatspace" jobs probably actually require more logic and mathematical knowledge than Bob churning out stupid, unoriginal comments or "opinions" on social media.
Most likely he'll never actually "improve" and evolve up from the laughing stock that he currently is (as in, actually reading any book on any subject he talks about written at a level above the 6th grade or average social media writing level), since 99% of his "world" as is would be bust, and he'd be forced to more or less retract 99% of the "comments or statements" that's he's wasted years of his life on marketing as a "progressive job or career", when it's more akin to a "celebrity gossip" author like Perez Hilton wrapped up in a "nerd or geek" veneer to appeal to mouth breaders who identify with "geek chic" but in reality have less knowledge about anything remotely mathematical than the average plumber or carpenter does.