I don't disagree at all, and a lot of it is on the workers themselves. In the music industry, having a great band photo is as much of a part of your press pack than the music itself, if an actor doesn't have a decent headshot, he's never even going to get roles in student films.
But lets be honest, so many of these shows have several photographers roaming around; just line the workers up against a bright wall and take photos that the promoter can then use for the posters.
If you respect yourself and the business so much that you will spring $500 for gear, you can pay someone with a good camera an extra fifty and get a good headshot. It's part of your package. Heck, most homes have high def cameras that you can take good stills on.
I'm not saying it's solely on Lamont, of course not. I know him and I know he puts in a ridiculous amount of work on his shows and on his students (which in turn makes the shows better), but for an outsider, a poorly designed (or overdesigned) flyer can turn a potential customer off. We all know this.