Does Bob even want to leave his beloved Bahstan? Despite its historical significance, Boston is not exactly a cultural center of the United States. There are very few--if any--productions there except perhaps
Ghostbusters 2016 (and we all know how well that went down) compared to New York City (thriving theater and television scene) and Los Angeles (film and television.) Hell, Canadian cities like Vancouver and Toronto are more culturally active than Beantown.
That will always be another hilarious trait of Bob. He believes that he's an industry insider and influencer because he talks about pop culture from a moldy basement. The truth is that he is another outsider looking in like the rest of the plebs. As
@Mola Ram said, he wouldn't get past the doorman at a Manhattan cocktail party and I seriously doubt Bob did or ever will rub elbows with celebrities at Comicon in San Diego. Being an anonymous member of the crowd in Hall H will probably be the closest he will ever get to that.