daydreaming and doing are two different things. I know i've had my fair share of trying to touch the wheels on the corn, only to have to pull up for the telephone wires, great fun. Also remember looking back and seeing a cop tailing me once while doing the same stupid stunt. But on the same note, there was nothing around, and w/ the airspeed we were never in a situation where we couldn't complete a safe landing given an emergency. So same note.
Flying over you school isn't a crime, flying lower than the second story windows while you buzz the quad could be considered one. And while TP isn't going to do any "permanent" damage to anything (faa doesn't specify whether it has to be permanent or not) paintballs into the side of your fender at 90 mph probably could put a dent or two, and that would definitely be a violation.
I'd vote for suspension, if he sees it, he probably wouldn't do it again...Just hope he was able to learn form this, and convince the Airforce that he has as well...cause this stupid prank wouldn't be worth throwing an academy experience away for...i'd be kicking myself for the next 18 years.