Read it. Then don't read my carping comments below.
I humbly assert that this is an excellent essay. However I will only comment on the parts with which I disagree.
1. A cruel parody of the first two thirds or so of the essay is "When I came to Washington I wanted to disrupt life for comfortably cartels of producers. Now I realize that pre-internet journalism was one of them. It is fine to make life uncomfortably for airline workers (including executives) but not to make it difficult for people like us." Surely you can see the pattern of a young idealist who works for very little and wants things shaken up becoming a not so young exceedingly established retired dean who thinks things have been shaken up to much. I don't think this is fair at all. But I enjoyed typing it. 2.Assange is a journalist. Manning is his source. Assange did not publish huge amounts of classified material by pushing a button. Wikileaks screened the material. Yes there was too much for them to screen, so they collaborated with newspapers. But journalists Wikileaks, The Guardian and The New York Times were doing the same things. Those at Wikileaks were paid much less (if anything) and are not members of the club. That is the difference. You'd really better update before Glenn Greenwald reads this post. He can be very harsh. 3. "What if it turns out that journalism’s social mission and its economic fortunes have simply diverged—that ventures like Klein’s do a superb job of informing the public, but don’t make money? Should we just shrug our shoulders and say, Sorry, if the market won’t support you, you shouldn’t exist?" "Superstar". There is a radical contrast between your guess about the economic fortunes of Ezra Klein and your guess about the economic fortunes of Ezra Klein. I think it is clear that the economic prospects of his venture are solid (ask Josh Marshall). Wonkblog shows how much it costs to produce excellent journalism (very little).
I think the problem with daily Newspapers and TV news is not principally financial (although the financial problems are extreme). A profession which can afford to send hundreds of well paid people into a room to shout questions at a press secretary does not lack enough money to do a better job. You briefly note that the Washington Monthly had a budget of roughly zero (and probably still does). It gets the job done. To choose a middling example CNN has a rather larger budget. It doesn't get the job done.
4. "There was some of this feeling in President Obama’s State of the Union address this year, which evinced a deep weariness with the process of seeking legislation and a preference for executive orders, or for Congress to present solutions to him, rather than vice versa."
I disagree entirely. Obama is smart and idealistic and a wonk, but he is not a technocrat. He clearly is inclined to seek common ground and try to find solutions together. He turned to executive orders, because it was obvious to him (as it is to you) that he can seek legislation all he wants, but there won't be any. Clearly this is a case of someone who loved Democracy not wisely but too well finally facing the plain fact that, however wonderful it might be, the legislative process will not occur in the near future except for keeping the lights on and the debt paid on time.
I am never convinced by "evinced". The verb to evince is rarely used and never used when a plain verb wouldn't make the claim clearly false. If we find something in a speech we can say it is stated or displayed or revealed or exposed. You wrote "evinced" because it is so weak a word that a sentence based on it can hardly be false. I propose that you ask yourself why you wrote write "evinced". I think it is because you wanted to make a claim, but knew it was false. Also the word "some" serves only to weasel. It has no meaning in context. It served only to weaken a plainly false claim to a not so plainly false claim.