Despite owning some of his books, I can't say that I am a fan of Gladwell's writing style. But his Revisionist History podcast (revisionisthistory.com) is, by far, one of my favourite things to listen to and I highly recommend to give it a shot.
I came to Revisionist History with a healthy skepticism of Gladwell. I echo your sentiments about its worth. The semi-connected episodes 4,5,6 from season 1 about education hooked me.
I also enjoyed Saigon 1965 (S01E02) and the one about McDonald's french fries but more importantly the beginning of the war on fat in America (S02E09).
He unearths some good perspectives in the podcast and it doesn't have the pop-sci feel that his books do that get my BS detector going.
I find Gladwell very entertaining and enjoy his podcasts, even his most recent one about the music industry (Broken Record) despite not even really caring all that much about the topic (He makes even boring stuff interesting!)
However I have to agree that he doesn't strike me as a writer that deserves to have a masterclass named for him.
I also have some serious skepticism about the quality of his insights and his journalism. I'm under the impression that he is "often wrong but never in doubt" as they say.
I had a really hard time with the podcast (season 1), but I'll queue up one of the newer episodes. I felt like I could have had 10 podcasts worth of observation combined into a one hour slot.
I feel that his podcast, like his books, promise more than they deliver. That said I had to actually buy/read/listen to them to arrive at that conclusion, so I am sure that Gladwell will be happy enough.