I think the best way to let kids learn how to manage their freedom is to actually give them some. We all see college kids who crash and burn first semester because they've never managed their bedtimes, assignments, meal choices, money, and invitations for booze and sex.
I think you start out with a weekend night when there is nothing major the next day. You can have some basic boundaries - no stove, no friends, no leaving the house, no using the fireplace, and so on. Have parental controls on cable stations and computers, of course. But if there are popcorn kernels and soda cans all over, well, then he learns the hard way about how very hard it is to clean up. That means vacuuming, washing dishes, collecting and rinsing cans for recycling (and oh, how much harder it is when food is stuck on after sitting overnight!), and cleaning up popcorn butter stains from the carpet. A tired kid who didn't get much sleep is just going to ADORE carpet cleaners and scraping caked-on gunk from plates.
You don't let him do it before a game, a test, a family wedding, or a holiday - but the surest way to teach him he needs his sleep is to let him be miserable when he doesn't get much. Life goes on and responsibilities continue - he can't take the night off and then take off the whole next day too.
You have to have a way to monitor internet usage, cable TV channels, and the doors. Simple parental controls and alarms will handle that. If he screws up, then you tell him he's clearly too immature to manage these decisions on his own. Set a target date of when he can try again, and a plan he needs to follow to regain your trust.
I assume you already go through any phone he has and supervise his computer. So go ahead and let him stay up, and while you should have some boundaries, it's not bad to give him a little room to screw up and learn the hard way.