I feel like his take on Pit, bringing pit into the modern world with smash bros brawl, then making pit have his own, modern game, that is so rich of detail and completely builds upon the existing worlds made sakurai appreciate character history and heritage even moreso than before. He could have scrapped all of the old enemies, but he kept them. He could have changed the enemy names, but he kept them. He could have rebooted the franchise, started over, but he made a sequel that takes place 20 years after the last game.
He completely learns to appreciate everything that fans like about the old games, learns how to remain faithful to that, and then learns how to make them work in the modern world.
Then, he reveals smash 4, with mega man. Mega man could have been more like his manga/anime counterpart, but he made him look like his 8-bit instead. His poses, his animations, his moves, all 100% faithful to megaman. Why? Because sakurai now has an appreciation for character IP heritage, all thanks to Pit and Kid icarus. Something he didn't appreciate before, because he was never tasked to make a sequel for someone else's game.
He shows donkey kong get his roll. He shows wireframe little mac. He shows link's back flip. He's starting to make changes that better reflect the character's history and heritage.
