“The ones that do stand a chance are the ones that are significantly, obviously different.”
Charging for regularly updated content is a pretty uphill battle. If I can get the Village Voice for free, or get a Times or Wired magazine for $10 a year, how are you going to compete with that? The problems are of scale.
Then again, charging for specialised content that doesn’t have to be rewritten every week (ie. keeps some value) is pretty doable I would think.