If he tries to stay past his expiration date (as you so aptly put it) expect to see him cast it as a “temporary” measure necessitated by “unique national circumstances”. Change often happens via the proverbial slippery slope.
Liberals will, if necessary, accept an incremental path toward achieving their goals. And make no mistake about it, they clearly want put the Constitution in the dustbin of history.
He may try something, but if he does, I think — or at least hope — that it would backfire on him and his true believers in a spectacular fashion. If there is a crisis of his own making, I think — or at least hope — that that would be obvious (e.g. disorder caused by ACORN punks), that in a country of over 300 million people a significant number of them would be ready, willing, and able to fight postponing the election, and that patriots among the political class would stand up to the plate and lead the fight. If there is a crisis not of his own making, who but the true believers feels comfortable knowing that the only man who stands between us and the abyss is Barack Obama?
I go back to my original point. We had a presidential election in 1864. How the rest of the war would be pursued, what would be done about the freed slaves, etc., were issues open to debate. The Democrats nominated Gen. McClellan. There were Republican leaders who opposed re-nominating Lincoln because they thought he couldn’t win. Some Radical Republicans bolted and formed the Radical Democracy Party, nominating John C. Fremont. Freemont offered not to run if the Republicans nominated someone other than Lincoln. Eventually, Fremont changed his tune and withdrew in support of Lincoln.
The process went on.
Unless we degenerate into a “Hunger Games”-style dystopia in the next two years, there is no reason for the election not to be conducted as scheduled. If we are collapsed and ruined, then the election is beside the point.