before he even gets close to the likes of Ric Flair and Shawn Michaels, he needs to develop his mic skills, charisma and personality ALOT. You can't just throw the next good wrestler, give him a push and expect him to become a legend. Legends take much more than that to be made.
I don't think he'll come close to HBK and Flair, because at least for HBK that's a ridiculous combination of everything. He was so good in his 2002-2009(?) career that I didn't even appreciate it (lol, expectations...), he was just acting perfectly the whole time, let alone his in-ring ability. I do think he'll be a perennial main eventer.
Btw, regarding your signature, I don't know when you put it up, but Bryan beat Kane clean at SummerSlam last yr with a rollup. And that's clean. Besides, I love weird finishes that are nonetheless clean if you can credit it to the winner's intelligence, and thus not to it being a fluke (see: Angle over Undertaker at No Way Out 2006 on weird reversal of the triangle choke).
WWE favorites: Punk, Sheamus, Lesnar, Ambrose, Rollins, Reigns,
Del Rio, Orton, Bryan, Ziggler, Wyatt, Usos, Cesaro, Mysterio, Kane DGPW: Doi, Yoshino, Tozawa, Yamato, Dragon Kid, BxB Hulk, Ricochet, Super Shisa NJPW: Okada, Nakamura, Styles ROH: Briscoes, Fish and O'Reilly, Young Bucks All-Time: Rock, Punk, Lesnar, Angle