My parents don't do the whole English thing. But I still got through it. And three years ago I was that guy that thought that ALL officers were trained at West Point. I didn't even know a thing about West Point, it was just that place where military people come from.
The beauty of the admissions process for all academies is that it can be successfully completed by any motivated candidate by themselves. Resources are readily available everywhere: BGOs, forums like this one, the local congressman, books, magazines, websites, etc.
If he wants it, he can get it.
The real question is, does he want it? A service academy is definitely not for everyone, and serious thought must happen before making a decision. It's good if he's having second thoughts; that means he's thinking.
Many service academy applicants will also be admitted to Ivy League schools and some of our nation's best public and private universities with full tuition ROTC scholarships. Would he still want the hardship that comes with service academy life when he's faced with a full ride scholarship to Harvard or MIT? By the time he graduates from high school, will he even want anything to do with the military at all?
If anything, try not to push hard. A nudge once in a while might be helpful (especially when the ol' senioritis sets in), but otherwise, just let him figure it out. Determination, motivation, and initiative is something he'll have to learn, and something the academies will demand. Make sure that he understands that his future is his responsibility.
Then, later, when he's faced with a crimson envelope from Harvard and a blue or black folder from a service academy, encourage him to make a sound decision before jumping in. I think that's the best thing that parents can do for a candidate.