Here's an idea: how about (in addition to replicating the paper online, which is a valuable resource) having an entirely different community site that is branded separately but relatedly. That might help management relax. Then aggregate blogs, hold forums, have polls, have very-local-weather reports, review movies, have the best possible community events calendar, create (simple, low-barrier-to-entry) virtual worlds, assign stories collectively, have photo contests, whatever. But in a slightly different voice.
One model I like is the Time Out New York offline setup. It's got the voice of an informal blog, with regular columnists, plus all possible information about all possible events. It's overwhelming, but I can imagine that the online Greensboro version might have a more manageable amount of information. Time Out Greensboro plus The Aggregated Voice of Greensboro -- with revenue coming only from large concerns placing listings. No subscriber fees or "premium" content that's hard to get to -- the friendly craigslist model.
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