The advertising industry is arguably one of the top 3 most creative focused industries on the planet, along with Hollywood and the music industry. That said the media covering the industry is about as uncreative and unexciting as can be. No offense to AdWeek or AdAge, ok...maybe a little offense, but they should feel an obligation to raise their games a bit if they want to be taken seriously as journalistic mediums. Take an editorial stand. Don't be so afraid of pissing off anyone that you write nothing but fluff pieces complete with "happy endings".
I know it's difficult. The people you cover are also your subscribers, but if you put out an interesting, creative and important editorial product, this industry that is starving for just that will eat it up. Once that happens, the advertisers will come in droves. It's how media works and has for over a hundred years. I think this space is ripe for someone to come out of the box strong and make a big splash. AdWeek and AdAge are best positioned, but probably won't as they have the largest existing franchises to hold onto. It will more than likely be done by an upstart, but it would have to be one that is well financed. MediaPost is interest, but clearly trying to just pump out tons of stories, regardless of relevance or importance, to create more advertiser space. The blogs are a start, but truth be told no one blogging has the embedded network or wherewith-all to get the real stories of interest and importance. Hopefully someone will come in a fill the gaping hole that currently exists. And if they do, I bet they'll make a ton of money on a few years and put a real hurt on the existing trade press players.