"The other point is that it truly doesn't matter if Tom feels people are wishing for us to lose in Iraq. In my opinion, we've already "lost" if one wants to define winning as ending up with this marvel of democracy in the region."

What country in the region [and you can even include France and of course Israel as one of these countries] out shines Iraq as a "marvel of democracy"?

There is a free press in Iraq. People voted and are represented by their people in government. They actually have constitution approved by voters [unlike the EU].

Iraq was worse off then some [or most] people expected. Iraqi were oppressed to a similar degree to what Soviet people were affected by Stalin and the legacy of that kind of policy. To their credit, the vast majority of Iraqi did not like Saddam, the same can't be said about the Russian people and their views towards Stalin. And the Iraqis will probably recover in a shorter time frame than some ex-Soviet populations- they are still severely affected and probably will remain so for further decades.
Iraqis do have potential of other people of the world seeing them as a great people they are, but of course they do have large problems that need to be resolved.

Much could be said about this, but first no one was claiming that within 3-4 years Iraq would be an America [assuming you think America is a enough of a marvel of democracy to fit your idea of what Iraq should have achieved to meet your idea of what was the "general expectations" or the implied general expectations by American leaders or "opinion leaders".

One reason Iraq was worse off than some people in the West expected was because we had news coverage which was corrupted by threats of violence and threats "reduced access" for these news organizations. Another aspect was that people in general feared for their life [and the life of their family] from the Saddam govt. A third aspect was a vast amount incompetence of the Iraq government to function in any way at all- e.g. public infrastructure was let to rot. And because of the lack of information regarding what a hell hole Iraq was, such a person as Michael Moore had a slight possiblity of selling the foolish idea that the "kiddies were flying kites" in Iraq meme.
Now, it is doubtful that Iraq was as bad as N Korea, but I would grant a possiblity of this being debatable; it might be a simply a matter of preference like how you would end up dead- by fire or ice. And N Korea might do a better job of being the worse hellhole if it had more money to use to oppress it's people- maybe Google should get over there to reduce to costs of oppression.