Here in Washington, many are jumping on the sale of the Washington Post as an opportunity to highlight the success of Politico as a missed opportunity. When I worked at the Post's web site in the early 2000s, the politics section was already one of the larger verticals within the site.
Part of the problem with sustaining a politics based site is the advertising cycles are very cyclical around elections. There were dozens of 'dot-bomb' era efforts that hoped to capture just a portion of the online advertising, then would have to lay people off after the election was over. The fact that Politico has become a moderate success is the exception rather than the rule in my mind. While Politico may have done well in the 2012 election season, they need to survive a dry spell at least to get to 2014 in my mind. In theory, you could say that the Post missed the chance to launch PTI by letting Tony Kornheiser and Michael Wilbon go work at ESPN.
At the same time, since Politico has launched, the Post has built a Wonkblog site around Ezra Klein and a small team of bloggers, and more recently a tech policy blog. So it is not as if it has ignored the success of Politico. There was also a previous iteration of the tech policy concept called WashTech, which was eventually shut down. The Post even hired writers such as Joshua Topolsky of Engadget and The Verge to write a column in print. But the Wonkblog model seems to be more viable, as ESPN has sort of done the same thing with Nate Silver, and to some extent, the New York Times' elevation of Andrew Ross Sorkin.
If anything this seems to be the model of the moment. The Atlantic has done something of the same thing, partnering with Richard Florida to launch its Cities site. But the Post hiring some one like Topolsky or Barry Ritzholtz to write something for the 'dead tree' edition on weekends doesn't do much for me.
Here in the Post's own back yard, the Marginal Revolution site has a fairly passionate following. At least online, I'd like to see them elevating some like Tyler Cowen to the level that the Times has with people like Paul Krugman. I also would like to see Jamie Mottram doing something on the sports side, as he is a native Washingtonian. Tim Stevens also comes to mind as the person who most recently left Engadget.
Lastly, the Post is late to the game in erecting a paywall. Part of me thinks this is a mistake, as sites like the San Francisco Chronicle are actually abandoning their paywall scheme, which I'm guessing wasn't even breaking even. Building the e-commerce backend around a paywall isn't cheap, and you are certainly going to see your ad impressions go down, so it doesn't seem like a great idea for a mid-tier newspaper to spend all that money hoping that paid subscriptions stop the bleeding. Even Andrew Sullivan's paywall adventures have been far from a grand slam, and he has a relatively large following.
If I want to pay $100 a year for news content, I will subscribe to the Economist. But if you offered me a $4.99 per month plan that gave me full access to the New York Times, even with a little advertising on it, I'd probably do that. If that doesn't pay for itself, then I probably would say don't bother with the paywall. Would I rather pay $80 a year for Amazon Prime or a subscription to the Washington Post? Pretty sure I'd rather have Prime.