If you've ever seen "A Beautiful Mind", Russell Crowe's character ends up winning a Nobel Prize for a breakthrough in choice theory that is traced to an experience he had in a bar as a young man with his buddies. Several attractive young women are gathered but one is clearly the most attractive. All the guys train their sites on her, except the lead character, who correctly figures that if he shoots for bachelorette # 2, he will have a clearer field and thus, more success. (And by the way, if you hadn't seen # 1, # 2 would've knocked your socks off in the first place.)
UVA applies this thinking to recruiting. Obviously, they want top guys, but they stop short of recruiting those they project as possible first rounders. O'Connor has said publicly that he refuses to tie up his scholarship budget on kids who will then go pro out of HS and leave them scrambling over the summer. In this, UVA differs substantially from, say, Arizona State or UNC, who make a habit of trying to land recruits at the very top of the charts, then doing their scrambling after the smoke of the pro draft clears.
UVA also prefers to recruit depth. So, they refuse to get into a bidding war for any one player. I have not heard of them making offers in the 80-90% range to anyone. They spread their money more. If you pursue UVA you will hear them say, "When you are ready to commit to us as your top choice, then we will talk money." They want to get you sold on the school and the program first, then see if you want it bad enough to take maybe a bit lower % than you might get somewhere else. Besides, if you're in state, it's still a great deal financially.
A 2005 Richmond area kid, then ranked # 4 nationally by PG, was passed over by UVA, and many at the time asked why. Three years later, Greg Miclat, the guy UVA got instead, has far outperformed that kid thus far.
I'm not saying this is the only philosophy that works, but clearly this philosophy does work for UVA. Whether it works for your son, now, that's going to depend on where he stacks up.