You make valid points. I suspect that there is more info on the heads up classes simply because the rules are more narrowly defined. In the bracket classes, all that matters is your et, not what it took to get there. There is no cheating in the bracket classes (other than the sandbagger), but...
He's off to a great start. Make sure he studies music theory, learns his scales etc. Definitely keep it simple. Don't play everything you know on every solo. Keep 'em wanting more! Good luck and most of all have fun.