As much as I won't apologize for advertising and trying to monetize my sites, I'm far from happy with the quality of said ads. Most of it is crap, the fill rate sucks and the CPM's are sad. I do get a few self-sold campaigns with various advertisers every year, but they account for only 5% of total revenue.
That said, I was contacted by Federated Media, who handles ad sales for Digg, Boing Boing, GigaOM, Revision3, Fark and other new media darlings. Our audience for CoasterBuzz is tiny by comparison to these sites, but the prospect of getting quality, non-annoying advertising could be a huge boost to the site. It sounds like they're ramping up a travel channel.
It's also a nice feeling to be recognized for a certain amount of legitimacy, and after nearly seven years, I should hope that comes naturally by now. Honestly that's the thing that has always been one of my greatest concerns. I've got the ears/eyes of industry types almost despite the enthusiast slant, but got there by focusing on the news that the trade rags were too slow to deliver. I do think that I have to make a decision on whether or not to start a new brand, more industry focused, but that's expensive unless I can sell ads to industry vendors.
The gears are certainly turning, that's for sure. I can't stand floating between hobby and full-time job forever.