Despite his many advantages in the 2012 election, Obama has two big problems to overcome: money and voter suppression.
The US Supreme Court's Citizen United ruling pretty much opens US elections to unlimited campaign spending. Political Action Committees (PACs) can be set up by private citizens or corporations, can take donations anonymously and have no limits on their spending (a bit of an oversimplification, but only a bit). Since rich people and corporations are usually Republican supporters, Romney will get most of this money. Its possible the Democrats might be outspent 2:1 on all races in the November election.
I think team Obama's unusual spending this summer is an attempt to offset the money problem. Usually, the real money doesn't show before Labour Day. But this summer, Obama has spent a ton ($40+ million) of money on negative ads in swing states. Despite the poor economic news recently, the national polls show a small shift in Obama's favour. So the attacks on Romney's character and business record are resonating with voters on some level. I'm guessing team Obama is front-loading its spending in an attempt to define Romney before the tidal wave of Republican money in the Fall. If they succeed in creating a durable negative image of Romney, it could work.
Money is a well-known quantity in elections. Voter suppression less so. The tactic is nothing new, of course. But Jim Crow laws were used mainly to ensure white only candidates and voters for State and Congressional races. They were never an issue in Presidential politics until the 1960s. Since 2010, Republicans have been using their positions in state government to pass restrictive voting laws in an obvious attempt to disenfranchise Black, Hispanic and poor voters. While States have long been able to get away with discriminatory registration practices, there has never before been a large effort to actually purge minority voters from the rolls.
Universal suffrage in the US has only been around since the late '60s. You'd think Americans would resist attempts to roll it back. And you'd think the Democrats would have figured out ways to counter-attack. Especially after the shenanigans in Ohio that cost John Kerry the Presidency in 2004. Current and pending lawsuits in Federal Court may overturn some or all of these laws in key states. Or not.
Even with these issues, I think Obama will win. But it may be very close. If the lawsuits fly over voter suppression in the fall, the Courts may decide the election, again.