I don't know that I would even want coverage from Techcrunch, for either myself or you. It warps your perception of what provides value and what your goals are. For example, you might spend months worrying about getting featured by fickle tech publications when you could be providing news to Chicagoans.

It is wonderful that you've got a site which journalists are using as self-promotion engines. Now you have to figure out a way to get their core use of the site to be a you-promotion engine. The traditional way to do that in journalism is original reporting, which means they have to cite you. They probably won't appreciate that -- you'd be competing with them, after all.

On the other hand, if you had some sort of scoreboard of the most influential reporters in Chicago, I guarantee you they would fall over themselves to cite that, particularly for the ones who ended up winning.

(Note that this puts them in exactly the position you are vis-a-vis Techcrunch right now. "Dang, if they would only cover me I'd finally get the respect I deserve from my editor! Please cover me! I wonder why he won't cover me? Is it something I said? Can I call him or would that be forward?" I know which side of the unrequited obsession I'd prefer to be on.)

Tell me, Windy Citizen, who is the most influential columnist in Chicago right now? You are, after all, the paper of record for the papers of record. You can take a page out of your customers' books and give them a nice little plaque (or badge for their site, focused again on promoting them, not you) for it if you want -- is there a single hotdog stand in Chicago which does not have a "Voted Best Chicago Hot Dog 1992 by the Reader" in it?

Ideally you'd be using the highly competitive journalistic impulses to provide more, better news to Chicagoans rather than just playing inside baseball with local media.