Remind me how long those Championship reigns lasted again.
I'm not saying that he didn't have moments that were special because he did, anyone can see that. My pint is that he really made it count. Can you honestly say that the WWE got what they should have got out of him? Every time they put stock in him, he got injured and failed to deliver. He is nowhere near the level of your Hogan's, Cena's, Rock's, Austin's, Triple H's... Honestly, the discussion isn't even there to be had.
I respectfully disagree. He needs to go in WWE Hall Of Fame for his run as in Hell No and Yes! Movement. Not to mention that he is a great in-ring worker and a good story teller. He maynot be near the level of guys you mentioned but still he is fully deserving of a HoF induction because HoF is not only for Hogan, Cena etc. Bryan does a special unique place in HoF.
As for the OP, I think Wrestlemania 34/35 would be a right time.