Glenn's job is probably easier than yours in many ways at this point. He has a system down, he has a venue, he has his support team, he has equipment, he has experience, he has a validation in many bands eyes, he has a loyal following, he knows he's going to sell decently well, etc.
But I'm sure he still has a million stresses that come with finding bands, booking bands, dealing with bitchers and moaners, dealing with overpriced hotels, and logistics.
Those dates are pretty good. Based on who you get I know I'll try hard to go.