I think the military is a great way to help fund (or in some cases completely fund) college. The potential long term benefits to the young man are greater than just money.
But having said that, and despite what the recruiters say (I was one many moons ago), the Army isn't for everyone. Does this young man have the personality that will adapt to tough discipline and working under somebody else's schedule on a daily basis? Could he adapt to living in a tent for prolonged periods and complying with strict rules regarding personal appearance and personal behavior?
For some late teens who lack adult counsel or whose maturity level make them succeptible to world influences as distractions, the military can be a great way to motivate and give a sense of direction....but for others it can be a source of frustration and dread.
Our youngest son enlisted at 17, and the Army, despite an Iraq tour, has proven to be beneficial to him in providing him with motivation and organizational skills. As to education funding, he signed up for the infantry, so he qualified for and used the $30,000 GI bill (not sure what it is today), and then when he finished his enlistment, he joined the local Army reserve, who then paid for all his upper dividsion college courses at the University of Utah, where he graduated a couple of years ago and now has a good job. He finished with zero loans and had a reasonably confortable life while attending college. For him, it worked out perfectly.
But having served a career in the Air Force, I can tell you from personal experience that there are, on occasion, young people who enlist that have no business being there. They hate the structure and bureaucracy and despise others dictating to them how they'll conduct themselves. For them, the 4 year enlistement was a frustrating waste of their time.
So I think the military as an alternative for college funding should be a decision that is about more than just the money.
BruceM