Ashley Hall's strength always used to ebb back and forth. When I played for them in middle school, we had a handful of Fury members and made it to the playoffs. That was also back when Pinewood was not a real contender; the big powers were HHP and upper-state schools like Cardinal Newman.
I do know that almost all of my challenge/premier teammates elected against playing for Ashley Hall Varsity while they were there, so while Ashley Hall the school may actually have enough talent to be a decent player in the state, that doesn't necessarily mean that all of those talented players are going to come together and play. The program doesn't have that kind of weight there like Wando would.
At Wando, if you're a top player, with a few exceptions, you play for the school because the program has a reputation. Ashley Hall's program doesn't have the pull to entice people away from a break or private goings on. Also, do they even have a serious coach or is it still like it used to be, with whatever teacher volunteered?
You do what you can with the personnel you have and since nobody likes to lose by a lot, I can't blame them for doing what they could.