Most of your last paragraph about Twitter is what has caused me to think he's dumb, in spite of having a few early successes which may be attributable to survivor bias (you have millions of people taking random risks, some of them are going to pan out randomly, and after the first one you have money so it's easy to make more money). Calling the rescuer guy a "pedo guy" during the crisis in Thailand and just myriad other inane utterances have tanked his valuation in my eyes.
But I think I might agree with you that "dumb" is the wrong word. Perhaps "unwise" is what I'm feeling. He may have skills and intelligence to apply those skills to start businesses or make money or whatever. But he doesn't apply that intelligence to the end that we might call wisdom, and I think that's what I as well as a lot of other people are trying to articulate when they say he's dumb. Agree with you though, people aren't black and white.