People give Sakurai a lot of **** because of blah blah tripping or whatever, but the man is a genius. People forget that, you know, he was the one who came up with Smash Bros in the first place. He's a brilliant game designer (started at 19!), and he has introduced numerous innovations throughout his career. His games are always packed full of content, incredibly polished, and completely unique. What other multiplayer games even play like Air Ride? Regardless of the mistakes he's made, or the ways in which his design philosophy may clash with the desires of the competitive community, Sakurai's retirement would be a tragedy. He, in my opinion, is in the same class as people like Miyamoto, Gabe Newell and Hideo Kojima in terms of "getting" game design in a way that countless others don't.
However, I do not see him retiring any time soon. He's a workaholic who loves what he does, and he's not very old at all. He's only 43, which is a ludicrously early time to retire. Yes, he has crippled both of his arms because of his insane devotion to work, but what he needs is a nice long vacation, not retirement. I don't think retirement is on his mind at all. And even if his arms cause issues, he can still direct a game. A big reason why he's injured his arms is because of his insane desire to contribute large quantities of the programming too. He just needs to be willing to dial things down and distribute labor a little more evenly.
But will he direct the next Smash Bros game? Most likely. Iwata announced that Sakurai was directing Brawl before he even asked him. He's a Nintendo MVP, even though he's freelance now. They will go to him before anyone when the time for Smash 5 arrives (and it will), and despite the clear fatigue he is feeling with directing this incredibly stressful series, I doubt he'll say no. One, he strikes me as kind of a pushover when it comes to Nintendo, honestly. Two, it's his baby, and if his reluctance to even let other people balance hitboxes is any indication, he probably wouldn't be crazy about turning the entire series over. Three, he and Iwata rose through the company together and are friends, and even though he's left Nintendo, he has a long history with the company. Four, I can only imagine how much he gets paid for this ****.
However, I could see somebody else taking the reins. I don't think that would necessarily be a good thing. I think a lot of the polish and creativity that we're used to from this series would be gone. People fail to realize just how singular Sakurai's influence on the series is. Sakurai is Smash Bros. Sakurai is Melee too. Everything that people like about that game, everything that went on to thoroughly inspire Project M, came from Sakurai just as much as tripping and coin battles. I think the temptation for a new director would be to completely cave to fans and give us a ridiculously unbalanced 70 character roster. Sorry to say, but a Nintendo produced game with a primarily competitive emphasis is never happening again, so we'd likely get the other extreme. That game would certainly sell, but would it be worth playing for years and years? I'm actually glad that Sakurai has the confidence in his own vision to sometimes give a middle finger to the fanbase. If years of hanging around this community have taught me anything, it's that a lot of us are at least mildly ********. I would never want to see most of you guys design a game, no offense.
But Nintendo is never going to "replace" Sakurai so long as he is still alive. So long as Iwata is around he's set, and even a new President would be able to recognize that Sakurai's name is synonymous with the series. The only way that Smash 5 gets a new director is if he says no. They will always go to him first.