Um, wow. That my friend is A LOT of coach flying over a 3 day period. Best of luck to you.
If you don't mind me asking - You don't state whether you have status with DL. Curious how you plan to shower after leaving MSP and arriving SIN before turning back to NRT 6 hours later? Do you plan to get a hotel room? Same with your semi longer 8 hour layover in ANC.