President Obama is preparing to kick off his 2012 campaign in Chicago this week but this time around, he already holds the job he's running for. That dynamic could prove to alternately be a curse or a blessing for his candidacy.

During election season, presidents who run for a second term must balance the public view that they are using their office for political reasons with carrying out their official duties.

"Politics is politics," Dr. Larry J. Sabato, Professor of Politics at the University of Virginia, tells Fox. "Everything a president does is political and all of it arguably affects his reelection chances."

Controversial decisions such as waging war or how to handle an international crisis can tip the scales in either direction. "Look at Jimmy Carter and the Iranian hostage crisis in 1980," Sabato notes. Carter lost his re-election bid that year after failing to secure the release of dozens of American hostages being held in Iran.

"Look at George W. Bush and the Iraq War in 2004..." adds Sabato. In his reelection campaign, Mr. Bush was judged on, and perhaps defined by, his decision to go to war with Iraq. He readily assumed the mantle of wartime commander-in-chief and won re-election.

Success, failure, or the perception of either can be a defining moment for a president's reelection chances and, Sabato says, how he plays it can be just as consequential in election season. "Even when you try to separate out politics, you are accused of playing politics, and the opposition party naturally suspects you are trying to pull an 'October surprise'," says Sabato.

When the president flies on Air Force One to Chicago Thursday for campaign-centered events, there's likely to be the usual talk about ensuring taxpayer money doesn't pay for the ride. Obama's press secretary, Jay Carney, was already asked about it in his press briefing Monday.

"There are no official events on [Obama's] schedule that I see," said one reporter. "Does the DNC pick up the cost for the trip?"

Carney said he'd check on that question, but it wouldn't be unprecedented if the president did decide to throw in an official event. Whether their aides say the reason is cost or not, presidents often pair campaign and official events on road trips; which helps off-set costs so the taxpayer foots some of the bill.

Should Mr. Obama choose to engage in purely political events on his trip Thursday, campaign finance regulations state that travel fees will fall to his campaign. "If a Federal candidate travels on a government-owned aircraft, including Air Force One, for campaign purposes, then his campaign committee must reimburse the government for the cost of the travel" using a comparable aircraft rate, according to the Federal Election Commission.

Those charges are not inclusive of the security required to protect the president. According to the FEC, "[T]he regulation provides that the 'comparable aircraft' used to determine the reimbursement rate would not have to accommodate any 'government-required personnel and equipment'," like Secret Service staff or security devices.

Still, the costs could add up for Mr. Obama over the course of a long campaign. However, with recent fundraising trends causing some to estimate that the president could raise up to $1 Billion for his reelection bid, his campaign could likely bear the burden.

Besides, the financial strain could be worth its weight in votes. "[N]othing beats the majesty of Air Force One landing somewhere. People line up just to see 'The President'," Sabato points out.

Take George W. Bush's dramatic Marine One landing in the middle of a baseball stadium packed with supporters in late 2004. The power of such optics is incalculable. Meanwhile, "a challenger has to build all his own crowds," Sabato says.

President Obama will even have to watch what says now that he's a declared candidate. If an event is not by definition political, he has to walk a fine line. "[U]nder law, certain activities are clearly defined as campaigning (such as soliciting funds or giving purely campaign speeches)," says Sabato, "and the White House legal counsel is the one charged with working with the campaign and making sure a president and his staff follow every regulation to the letter to avoid unnecessary, distracting controversies."

Given the myriad of guidelines and opportunities for missteps, 2012's President Obama is embarking on a decidedly different venture than that of 2008's candidate Obama.

For more on candidate Obama's promises kept and broken, click here.