I think the tavern brand has been established already, whether or not we like the aesthetics of it. But maybe it could be exploited. Are there microbreweries using WP? Would they like to advertise? Would they like to sponsor WP events like WordCamps? Lots of WP users seem to like beer.

I'd probably start by breaking down all the jobs involved in running the site into an org chart and then finding ways to delegate, and creative ways to reward people for taking on that responsibility. In fact, invite people to come up with what they'd want as a reward, and how they could get it, like having a membership theme club donate a membership to the volunteer in exchange for advertising space.

Some people will help just because they passionately want to see a certain thing on the site. Others will need some kind of compensation for their time--but that might just be advertising for their *own* services as WP consultants. You've got lots of ad space built in here already.

Finally, I tend to agree with the people who say you should look for a niche that's not being covered on other WP sites, or at least eliminate anything that feels too much like duplicated effort to you. If there's something that someone else is doing better, let them. But if there's something that no one is doing at all, and you and your readers are both interested in it--that's worth pursuing.