As for the awards themselves, Michael Chabon said, "Have you seen the McSweeney's?" when his Escapist anthology won, which pretty much sums up my feelings on a lot of awards. It's not that what I feel is the best book as a critic never wins Eisners, but it's more like it seems that the Eisners are always given to whatever comic brings the most pleasure in any way as opposed to the one that reaches excellence, which is a perfectly fine standard to have as a reader and kind of a sad one to project as an industry.
The Eisners are kind of weird, because they try to encompass a wider-range of material than most pop culture awards. For example, the Best Single Issue category included nominations for both Ex Machina--a high-concept super-hero entertainment--and the latest issue of Eightball--an artsy-literary comic. This is a kind of mix you'd never get with, say, the Oscars, where the equivalent situation would be the latest Spider-Man movie vying with the latest Jim Jarmusch movie for the Best Picture award.
This would never occur at the Oscars, because Spider-Man movies and Jim Jarmusch movies don't even get nominated. A Spider-Man movie might win a kind of Viewer's Choice-MTV-style award and Jim Jarmusch might clean up at Cannes, but, as far as the award scene goes, these two kinds of movies will never compete head-to-head.
This year, Eightball beat Ex Machina, so art trumped entertainment or excellence prevailed over pleasure, in this category, even if the Escapist vs. McSweeney's contest went the other way. And really is this so bad, or, as Tom puts it, so sad? I don't think so, especially if we consider the alternatives.
Take the Academy Awards, for example. By and large, the films that are nominated for and win Oscars are those that the Hollywood establishment deems "worthy", with worthiness being decided by a mixture of the movie's social relevance, its box office success, and the behind-the-scenes Hollywood politicking of its producers--a movie's "excellence" often has very little to do with it. The Academy Awards often seem to value a kind of fake piety more than they do excellence, which is a lot sadder, not to mention less honest, than when the Eisner Awards put pleasure over excellence.
Of course, you could always argue that the Esiner Awards should be modeled less on other pop culture award programs and more on something literary and prestigious, like the Booker Prize. But the problem is that the comics industry is still primarily a pop culture industry, and it isn't likely to change anytime soon. A literary prize-type situation just doesn't seem all that appropriate for an awards show that takes place at the San Diego Comic Con.
And, even though Will Eisner had great literary ambitions for comics, he's the guy who made his name with The Spirit, which is still considered by a lot of high-brow, excellence-loving comic book aficionados (like the folks who put together the Top 100 Comics Journal issue) to be his best work.
Personally, I think the Eisners are fine as is. They are far from perfect, but compared to Oscars or--even worse--the Tonys, they don't look all that bad.