This is a great question so I've given it some thought. Apologies about the long post.
I'd have done what Mike planned to for his TII era album, releases 3 maybe 4 singles over the course of a year and then add 7 or 8 tracks and release the album in time for Christmas.
I'd have gone for,
Whatever Happens late 2000,
Break Of Dawn March 2001
You Rock My World June 2001
Xscape September 2001
Butterflies late November 2001
Album release late November 2001
I'd have started with WH, to capitalise on Santana's popularity around 99-00 and because it's a mature sound for Mike. The same with Break Of Dawn, it's something the general public wouldn't have expected from Michael. Then release YRMW, typical Mike sound to bring in the summer. Xscape to round out the hype for the album, it sounds like Mike but feels fresh and modern. Then Butterflies in time for the release of the album to show of Mike's vocal ability and the diversity of the music on the album
Release short films with each of the singles and then maybe have a documentary on the making of the album a couple of weeks before Christmas.