The Obama administration asked Congress on Thursday to authorize $500 million to provide U.S. military training and equipment to “moderate” Syrian rebels, a move that will undoubtedly edge the U.S. closer to direct involvement in the Syrian civil war.

Up until now, the CIA has clandestinely trained moderate rebels in Jordan and armed them with small arms. The U.S. has also allowed other countries to provide the rebels with anti-tank missiles.

A spokeswoman for the National Security Council said the new funds, if approved by Congress, would “help defend the Syrian people, stabilize areas under opposition control, facilitate the provision of essential services, counter terrorist threats, and promote conditions for a negotiated settlement.” But in a three-year-old conflict, with more than a hundred thousand estimated dead and now more rebel groups than some can count, what does $500 million buy you?

David Maxwell, the associate director of the Security Studies Program at Georgetown University, said some of the money will most likely be spent on logistical items, communications equipment and weapons, the standard fare for training unconventional forces like the Syrian rebels.

“We have to be careful about what kind of weapons we supply them,” Maxwell added. “We have to assume it is going to be lost and either picked up” by others, including the Syrian government or competing organizations.

While the renewed focus on the Syrian rebel groups has focused on material and training, Maxwell emphasized that the rebels’ success hinges on their abilities beyond the tactical level.

“We focus just on the fighters … but that part is really just the tip of the iceberg,” Maxwell said. “All of the organization and preparation that goes into supporting those kind of tactical operations as well as what comes next…can they organize government…and can they transition to legitimate leadership when [Syrian President Bashar] Assad falls?”

Extremists groups operating in Syria, including the Islamic State of Iraq and Syria (ISIS), have been extremely capable at governing the territory they have seized. For the moderate groups to be successful, Maxwell asserted, they would need to be just as proficient as ISIS.

According to a current Army Special Forces noncommissioned officer who has trained local forces in both Iraq and the Philippines, the new training program for Syrian rebels, which will most likely take place in Jordan, will face inherent difficulties if it is not co-located with the rebels on the battlefield.

“Providing assistance is less effective when there is no support to operations,” he said. “That will always be less effective than training them up and then being co-located with certain elements.”

It’s also unclear how many rebels the U.S. military will be able to train at one time. Special Forces routinely train entire units at a time, but due to the battlefield conditions in Syria, they likely won’t be able to do so.

“It seems like it would be difficult to pull entire units off line in order to train them outside of Syria,” the Special Forces soldier said. “I think there has to be some element of train the trainer there.”

“Train the trainer” refers to training an individual or a number of individuals before sending them back to their respective units so they can train those unable to leave the front lines. This method is currently in use by the CIA’s program in Jordan, according to some reports.

In terms of training the rebels in battlefield tactics and weapons use, the Special Forces soldier added that literacy is a key factor. Low literacy rates among recruits have hampered training efforts in the past in Iraq and especially in Afghanistan.

For all the money and training about to be pumped into the Syrian conflict, many questions remain unanswered about the vetting process for rebels, the type of equipment being provided and what the groups will do if they successfully topple Assad.

“As the famous Beatles quotes goes,” Maxwell said. “Money can’t buy you love.”