1. We didn't go in with an exit strategy - many, many folks, including right here on FR, knew full well and stated such back at the very beginning that there would be ominous factions that arose to take Saddam's place. This has bore out as we predicted.
2. We didn't (aren't) fighting to win. To be fair, we haven't fought to win since WWII, which is why we have, technically, "lost" these last few actions, from Korea forward.
So, while Jeb is an idiot and this girl even more so, the fact is there is some truth in the statement.
To add to your list:
The idea that Iraqis (or any Muslims, for that matter) would in essence abandon their religion and place “democracy” (whatever that term means to anyone) in the form of a secular government above their supreme religious figure was naive from 4 separate standpoints:
1: The hardest thing to make people change is their religion. But this isn’t just “changing” a peoples religion; it was a proposal to have them renounce their religion, since to them, Mohammed is supreme.
2: There is utterly zero history of “democracy” in the Mideast with the possible exception of Lebanon and Israel (not what is being talked about) and the founders knew perfectly well that a foundational element for the establishment and sustainability of any such system is the so-called “civil society”. Without some inherent desire to establish and maintain a civil society, there is no hope for anything other than pure “rule of the jungle” or pure religionism in a society. There has never been any history of such a “civil society” in the Mideast. There are apparently functioning societies in the Mideast but without exception, they all function ONLY under the iron fist of a ruthless government. In other words: tyrranies.
3: That even if such an effort could be made to work in Iraq, it would never have been acceptable to any of half a dozen neighboring countries and thus secondary wars could be expected to erupt. Leading to an indefinite and unpredictably sized military commitment, perhaps on multiple fronts, if we wanted to preserve what we were proposing to “win”.
4: Ignoring all of the above, apparently without asking any creditable Islamic scholar or historian (never mind us mere civilians) who could have and would have immediately predicted these outcomes, was foolishly and willfully arrogant.