There's a reason why Obito stayed in the WWE longer than Itachi. He's got more talent, even if his angles got controversial later on. What it comes down to is this: Itachi seemed unbeatable, so nobody but the die-hard fans wanted him to win anymore. After his victory over Kabuto in Wrestlemania, they kicked him out of the business for good. Almost nobody was cheering. With Obito, he kept the crowd on their toes, even if they didn't like him... until he turned face, at least. Obito just has more talent as a wrestler than Itachi.
