2018

Who should win: Braun Strowman
Who will win: somebody else
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It's not too early to say that this year's winner will be wrong, too. Braun Strowman enters 2018 as WWE's hottest act after a breakthrough 2017. As a reward, he probably won't even be in the Royal Rumble Match itself, but feels like a third wheel in a triple threat match against Brock Lesnar, who he already lost to, and of all people, Kane.
With Braun Strowman likely gone and Samoa Joe's chances of winning almost as non-existent, the likeliest winner will be either John Cena or Shinsuke Nakamura.
A John Cena win would be terribly uninspiring, while Shinsuke Nakamura hasn't exactly set the world on fire.
People do want to see a match between AJ Styles and Shinsuke, though, so of all the realistic options, he's the best one, but he's certainly not the right winner.
As for the historic inaugural women's Royal Rumble, Asuka is the clear choice to win, as she's heading into it with the most momentum and has in only two months established herself as one of RAW's more over female performers. After last Monday's botchfest and confusing clean win over Alexa Bliss though, it's very possible she won't be in it at all and hotshotted to the title instead. That would be the wrong choice. It's still too early and I can't shake the feeling that it would be done solely for her to lose to Ronda Rousey at WrestleMania, which would be an immensely stupid decision when they could have a much bigger match next year.
Unfortunately, stupidity is par for the course in WWE this decade.