Its one of those great ideas that probably wouldn't work unless it came from the top (ie from Automattic).

If they arranged some kind of site, portal, or newsletter and invited the top WP experts and bloggers to contribute in return for backlinks that would probably work. Maybe you "pay" your way in to get something published by contributing to the Codex documentation as well. All pie in the sky of course, hard to work out how it would get off the ground.

Any third party iniative would probably fail for most of the reasons people already listed. Its hard to launch such a site and keep good content coming in without monetization causing disputes, and if you do it purely for free people will not give it a high priority and it will just die from lack of content.

I'm in the "would love to get involved but don't see how it would work" camp myself.