One piece of history that I'm interested in, but never see come up in these sorts of attempts to wring meaning out of the past, is the derregulation of major media rammed through Congress in 1996.
The lifting of ownership bans kickstarted a wave of consolidation across print and electronic media that gave us the doddering dinosaurs we all slag on today. Tribune Company, Clear Channel, McClatchey, et cetera simply could not exist in their present form if that bill hadn't passed. And my boss Sam Zell, telling the story of how he and Randy Michaels bonded at Jacor, said as much when he addressed our staff earlier in the year.
My suspicion is that the perceived economic incentives offered by consolidation and cost-cutting opened up by the 1996 dereg might have been too tempting in the short term for media executives to ignore. And why should they invest time and resources online chasing speculative new revenues, when they could clearly see immediate "efficiencies," "synergies," and other opportunities to increase profits through consolidation? Plus they got the rush of chasing business' biggest prize: The Deal. (Eric Klinenberg's book has some great reporting on how driven a lot of media execs were in that direction.)
So that's my long way of saying I'm interested in what degree the failure of the MSM to invest online was a victim of that opportunity cost. And I'd love to ask an executive who worked during the era as much.