So while Afghanistan oversees a major military transition, it also will have to make a political transition.
Who will lead the country during this critical moment in its history? Will the vote go smoothly, without violence and without controversy? There were reports of ballot tampering and other violations in the last one.
The answers might be just as important to Afghanistan's security as the readiness of its troops.
"The single biggest challenge for us is the political transition, the elections of 2014," said Saad Mohseni, the media mogul behind Afghanistan's Tolo Television. "(If) we have credible elections, I think we'll be OK for the next five, six years. (If) we don't, there is a real danger that we'll see instability, especially in 2014 as the U.S. troops withdraw."
5. What part will the Taliban play?
Despite the ongoing insurgency, Karzai seems eager to resume stalled peace talks with the Taliban and include them in the political process.
The Taliban pulled out of talks last year, but Karzai said last month they "are very much conveying to us that they want to have peace talks. They're also people. They're also families. They also suffer, like the rest of Afghans are suffering."
Javid Ahmad, a Kabul native now with the Asia Program of the German Marshall Fund of the United States, believes revitalized peace talks are essential to Afghanistan's future and to the legacy of America's war.
"If withdrawing responsibly in 2014 is indeed high on President Obama's agenda, then he has little choice but to prioritize and accelerate the peace talks, negotiate a cease-fire between all sides, and reach a settlement that ensures that the Taliban lay down their weapons," Ahmad wrote in a recent column.
But will the Taliban be willing to cooperate? And if they enter negotiations, how much of an influence would they have on an Afghan society that has seen so many changes in the past decade?
"There have to be some red lines," said Jawed Ludin, Afghanistan's deputy foreign minister for political affairs. "Some of the achievements that we've had in the last 10 years can't be negotiated."
Karzai sounded confident that most of the Taliban would acknowledge this.
"I think there is now a critical mass in Afghanistan of the educated, of the Afghan people who want a future of progress and stability," he said. "And I think also that the Taliban recognize that this corner has been turned, the majority of them. Some may be there among them who would not -- who would remain, you know, in the darkest of the mindset possible. But those are a few."