Unlikely there would be a duplicate thread as this one is pretty specific, although there are many similar topics floating around.
Well you can't treat this like any ordinary match so you have to be thorough in the preparations, because you can't just arrange this match on the night, you'd need a backlog of at least a month and sufficient advertising to make it worth it. Ok then, so firstly you have to consider this match from a logistics perspective, there has to be a worthwhile reason for dragging Rocky and Austin back into competition after so many years. So the story has to be up to scratch. I see you've go the idea of the similarities of the pairing in their respective generations and that it could work along this angle, so that's sorted.
Then you have to look at the parts on an individual basis. John Cena and Randy Orton both compete regularly and have no scheduling issues to allow them to be cleared for the match, no problems there. But this is where it starts to fall apart. The Rock and Stone Cold are both actors now by trade, and what's more it's their priority, so should there be a conflict in schedules between wrestling and acting, the acting will win. That's the first issue, there needs to be a time allotted so both mega stars can clear their diary for long enough to make it a possibility.
Then you have the ability and willingness to compete. Both Rock and Austin are out of practice, neither of them has actually physically competed in a full-length match since about 2004, that's seven years! So there's bound to be a tid-bit of ring rust. Now Rock is 38, he's in fine physical shape and not-competing for the last 7 years may have actually increased his shelf-life, I don't think physically he'd have much difficulty in out-performing Cena or performing to a satisfactory standard at least. Stone Cold, however, quit wrestling because he could no longer deliver the standard of performance his fans were used to, the years and bumps in the business had really taken their toll on his body to the point where he wasn't left any choice. So actually having Stone Cold in the match seems a bit difficult to say the least. Sure he'd LIKE to compete but with acknowledgement of the toll it may take on his body I don't think he will.
But the fact remains are they willing? Both men have said they had competed in their last match, I know the business motto is never say never but convincing both men to change their mind? It would require something very special to actually attain both men's willingness for a final match. I don't really think the match is possibly based on scheduling conflicts and shape of the competitors but that aside I don't think I'd want to see the match anyway.
I can appreciate Rock v Cena and Stone Cold v Orton as separate matches, the new guys win, go over with a huge rub and move on with massive momentum. But put together? That means is the fresher guys go over it's two of them with the same push, two of them? I don't see how that fits into the scheme of things. That's just me.
Personally I'd think you'd have a hard enough time getting Cena against the Rock, lets just take things one dream match at a time.