Your goals are to book a lineup that would (1) sell enough tickets to keep Bonnaroo alive, (2) improve Bonnaroo's identity (e.g. impress your voters) while (3) accounting for the type of acts the festival booked in earlier and later editions. More specifically, you should have three Bonnaroo sized headliners and subheadliners, late night shows, and genre diversity (jam, EDM, rap, indie, pop, rock, metal, country, comedy, cinema, etc).
Some guidelines about "realism": (1) consider how many tickets would be sold with your lineup, (2) assume you won't be given a budget to book three stadium sized headliners, (3) you are supposed to be booking for Bonnaroo, not a Primavera type festival - keep this in mind while picking your acts, (4) your Thursday lineup should be similar to how Bonnaroo books Thursdays - so it should mostly consist of "rising" acts, (5) The Other mainly books electronic/EDM/rap acts, and your lineup is expected to reflect this. You don't have to follow any of the guidelines here, but if you want to take the risk, it's up to you.