I think the single choices with Sony were almost flawless, so not to much to say for that era of her career except that "Underneath the Stars" should have been released (perhaps instead of or after "Forever") and "Can't Take that Away" should've never happened. "Crybaby" should have been pushed harder as a third single because that song is so classic. Post-Sony, there were lots of mistakes made...
"All My Life" (instead of "Loverboy")
"Lead the Way" (instead of "Never Too Far")
"Stay the Night" (instead of "Say Somethin'")
"So Lonely" (to end the Mimi era)
"Migrate" (instead of "Bye Bye")
"Love Story"
"Ribbon" (instead of "I Want to Know What Love Is")
"It's a Wrap" or "Candy Bling"
"When Christmas Comes" (was this actually released? I know it had an adds date but then I don't remember hearing anything about it)