TOD #2:
The show that keeps circling in my mind is Two Gentlemen of Verona (the musical). It seems to be generally dismissed nowadays, but I think it could still work for today's audiences just as much as any Shakespearean play. There's a couple of love stories with complications, mistaken identities and crossdressing disguises, many comical characters, high comedy, low comedy, social satire. And lots of catchy songs that easily lend themselves to all kinds of staging.
If I were doing this show now, I would take it back to its street roots. Cast mostly talented young unknowns, and keep the design elements to a minimum. Update some of the arrangements to include hip-hop and latino grooves. Yes, I think it would work.