There is no "he", he is a puppet controlled by a conglomerate headed by "them",
Soros and Ayers otherwise known as the oligarchy. "They" are much smarter than "he" is.
They know better than to pull a #2, that type of chaos only works when there is a certainty of overwhelming success. They know they are assured an unceasingly protracted battle that will result in a wasteland no matter the winner.
If there are handlers, how do we know the handlers do not want a wasteland? Real revolutions require Chaos - the destruction of the old, so the new can be ushered in. Once you talk of Handlers, you open yourself up to the full monte of NWO/Illuminati/Bilderberg/Alex Jones Conspiracy theory. Mittens also works for them, and disposing of Obama now just furthers "their" plans. How ambitious are they? Are they just Rothschild bankers looking for a new country to sink into debt and loot, or do they have more grandiose plans for a Socialist world government in mind? How would one know?
The existence of handlers really doesn't change the calculus much. We don't know "their" motivations or end goal, so #2 is just as possible with them at the helm as Obama's expectations would be set by "them", likewise with #4, as Obama would be expecting "them" to manage his fortunes for him. I think Obama is a true believer, but if under the influences of others, are they also true believers? If not, then what agenda are they trying to implement?
Given Borat's behavior as a clue to "their" aims, and assuming all that has happened so far has been going according to plan for them, taking over an intact and powerful United States and wielding its power doesn't seem to be on the agenda. Hence, leaving it in utter ruins, may be a side effect or the stated goal, but it does seem that is the direction they seem to be working towards.