There is no way that Hamilton at his best could ever beat Boitano at his best. Boitano, after his choreographic makeover, had it all. With the exception of his footwork, I've never seen anything exceptional about Hamilton's skating. I think the reasons he won so many amateur competitions is, 1. He was a stellar brown-noser and the judges lurve that. 2. A lot of his competitors (with the exception of Boitano and a couple of others) tended to crash and burn while he remained vertical. Doesn't mean his skating was all that, but he got lucky and managed to stay upright. 3. He was good at figures.
Scott's a great showman, but only a so-so skater.