@Gareth That really isn't how the scholarship's work here. It's either you make good grades or you don't get it. He may have quite a bit of support coming from his folks and the townspeople surrounding the school, but if he can't make the grades, he can't make it in the school. If his parents went to the school, they either should have money or have prepared him for a scholarship. As for having something special that would let him, he's a familiar, they're all unique. He could go to any other school to get taught, it doesn't have to be this one. So it's your choice whether he put his nose to the grindstone and studied for that scholarship, or his parents are actually wealthy enough to get him in that way.
Also, something about Aaron's personality is a little...contradicting. He's a guy that likes to stay in his shell and not show off in front of others...and yet around friends, co-workers, and even out in public, he'll try to pull practical jokes? He lacks confidence, and yet is always able to tell people the truth, even if it's something he knows they won't want to hear? Do you see what I mean?