> Get some of your chess team members to take temporary jobs on the crews setting up some of those shows
Bands travel with their own crew, so they'd have to get hired on as a roadie (which is not unskilled labor) where ever the tour was put together. Not so simple, because once you see the date at MSG, it's way too late to get on that crew, and if they do get on a crew, how would they know they're going to play MSG before the manager does?
I'm not certain, but I assume MSG is a union shop, so a local hire to work there would require joining the International Alliance of Theatrical Stage Employees (ISTSG), and being a productive member for years before having enough seniority to be able to choose where they want to work.
Promoters and event organizers hire temps (you'll notice young people wearing black shirts with "SECURITY," emblazoned on them at shows, the only unskilled labor available), but the first time they'd get to be on location is during the event, and they have to work.
While your plan sounds simple enough, the reality is it would not be possible even with years of preparation. You can volunteer in public theater or go to work for an event provider to further understand why, but I'll just tell you. There is too much competition from all the individuals that have made a career out of it as well as the exponentially larger group competing to land their career. How many chess team members have a degree in theater arts, film/video production, recording arts or communications? How many of these graduates do you think are able to make a career out of their degrees? It is insanely competitive. My understanding is to, say, get into set design at a venue in New York City, you'd need a Masters degree in set design and a metric shitton of luck.