My best guess is that the DO actually wanted the world Rand originally wanted to create, where the DO doesn't exist but ultimately wins. Of course, if that's the case then why does the DO go to the trouble of proving to Rand that such a world would be terrible?

In the end, the DO's actions, the actions of the Forsaken, and the cyclical and infinite nature of time all serve to make everything in the series incredibly pointless. You might even be on to something by saying that the stupidity exhibited by the Forsaken throughout the books is a cause of the Wheel forcing certain choices on them. Maybe in a similar way even the DO was influenced by it? The more he entered the Pattern, the more under its influence it became. I dunno, I just can't think of any possibility that doesn't make the Shadow idiots, or the entire conflict as good as won before it ever began.