If you are going to be intellectually honest, you have to consider what your opponent thinks and believes and why. I do not want Obama to win, because I love my country too much to see it continue on the destructive path he has set for it. But if you want Obama to take that long ride back home to Chicago in January of 2013, you need to think what it would take for him win, so that you can prepare and counter his actions.
The electoral landscape is not looking good for him right now. There is a 50-50 chance that we will enter into a double dip recession and no president has ever won reelection with unemployment above 8.2% for more than 70 years. Of course, no black man has ever won the presidency before either, so that tidbit is not necessarily governing but does provide guidance to be considered. With a poor economy, Obama can continue to blame Bush, but that story is wearing quite thin. The probability of a sudden economic expansion is highly unlikely, unless there is a complete reversal of economic policies. So that aspect is not one that he is likely to emphasize, and would prefer to ignore it if at all possible. It is further unlikely that Obama has the mental agility to even grasp how ineffective his policies are, so the chances of even recognizing that they don't work means that Obama will continue on straight ahead, heedless of the facts.
Obama is striving for a billion dollar campaign goal, and that is not necessarily unreachable, although a lot of the corporate bundlers who supported him before are unlikely to continue to do so this time around because he can't please all the big donors. Obama does have the fullthroated and unquestioning support of the Mains Stream Media, but their influence is also wearing thin as people come to realize that they are not honest brokers, but rather future Press Secretary wannabes. Alternative sources of information and commentary are taking over all but the most unsophisticated voters, and they will remain steadfastly loyal to the President if for no other reason than their unthinking hatred of the Republicans.
Electorally, Obama is still popular with 16 states, and certainly has the unthinking support of the 20% of the population that call themselves liberal, and that of the African American community as well. That base, assuming they don't stay at home out of disappointment, will account for 30% of the vote so he just needs to pull in another 21%. That is going to be difficult, unless the Republicans pull another weak candidate like McCain.
All of this seems rather pessimistic for getting Obama reelected, but there are two possibilities that can allow him to slip back into the Oval Office. First, the aforementioned Republicans pick the absolute worst candidate to run against him. At the moment, the generic Republican is beating him, but once the nomination is made, you can bet that all the political organs of the Democrat party will be mobilized to demonize his opponent. Doesn't have to be fair or accurate in the attacks, but if they are valid that will certainly help.
The other road to electoral success is the same one that Clinton used: A third party candidate that strips voters away from Obamas's opponent. Like 1996's Ross Perot, the third party candidate needs to be independently wealthy, have a certain level of charisma and the organization to get his name on the ballot. Dodnald Trump would certainly fill the bill plus he has the ego to try and make it happen. But I don't think that Trump will pull enough votes away to assure Obama's reelection. There may be a better candidate in Ron Paul. While he doesn't have the money of a trump, he does have the fanatical support of his followers who would vote against Obama if there is no other choice, but will abandon the Republican if Paul runs on the Libertarian ticket.
So in the final analysis, Obama can do little to ensure his reelection. It will almost assuredly come down to a third party candidate that is strong enough to pull more than 20% of the vote. Not that it can't be done, but it sure doesn't look good.