Sackboy
Chance: Highly Unlikely.
Sackboy is very cool and has a lot to pull from to make a very interesting character, but unfortunately we really haven't gotten a Playstation-esq/Sony-esq rep thus far unless you count Joker which is more Sega than anything else. While many others have said how unlikely it seems Sony would play ball, I find it to be much more likely that Sony WOULD play ball to get into Smash, but that other characters are of higher priority both in terms of marketability and fan request.
Sackboy doesn't really stack up to the likes of Kratos, Bloodborne Hunter and Rachet & Clank which Sony clearly values more during the early life of this console cycle whereas Sackboy merely got a platformer game and not even a true new LBP entry. In addition, Sackboy is likely competing with Nate Drake or the equivalent from Uncharted and while I don't think Last Of Us is the best choice for multiple reasons it still could be competition. He is also competing with the legacy of Pseudo-Playstation Stars like Crash, Spyro and Jak & Daxter, of which his request simply does not compete with, and that's with the rumor of new Jak stuff in the air.
If indeed we DO get a Playstation All-Star in Smash, the line is long and the odds don't favor Sackboy to win this Battle Royale.
Want: Minor Attachment.
I played the first two LBP games but I got into them late into the PS3's life cycle and I never messed with LBP3 just mainly out of forgetting about the franchise. I always enjoy games that all the community to make content in the game to share with others, but I never got into it enough to become really attached to it. Seems it didn't do well in numbers because Sony has cast it aside to pursue other successes. I always thought Sackboy was cute and I liked the narrator, but my love for the series kinda ends there.
Unfortunately, I have a bigger attachment to Spyro and Jak & Daxter and would much rather see one of them get in, and Crash, Kratos or Bloodborne Hunter would all be much bigger inclusions that would bring more hype overall, so I would be more excited to see them than Sackboy.
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Miles 'Tails' Prower
Chance: Somewhat Likely.
Tails is essentially #2 in terms of the most iconic and beloved Sonic characters, often placing above Knuckles, Shadow and Dr. Robotnik in terms of support and love within the Sonic community, which is fitting considering he
is the first sidekick/supporting protagonist introduced in the games. His design stands out and from a design perspective, between his use of limited flight and his many machines and tools over the years, there is plenty inspiration to take from to build him a moveset.
However, he has a major hurdle that I think is too high for him to fly over, but it isn't the Mii Costume: it's the amount of representation. We all know that Sakurai and his fellow Smash devs think differently from how us fans tend to do, and since Smash's inception each game has shown that the devs have different standards for representation for a franchise or games in the franchise than we do. Considering Sonic is the single best choice for a playable character out of all of the Sonic franchise, having stages, costumes and assist trophies from the series could been seen as 'having done enough', which would lead them to potentially pursue other Sega franchises in the future like Phantasy Star, Puyo Puyo, SMT, Yakuza, Streets of Rage, Jet Set Radio or many others from the Big List O' Sega.
However, Tails has another big problem and I think this wall really is so high that he would run out of stamina before he could fly over it, and that's that his own fans have given up on him. Tails's old costume was one of the first ones to return, and people are SO set on Mii Costumes killing a character's chances that his own supporters for Smash turned on him and started rooting for Dr. Robotnik or other Sonic/Sega characters instead. Not only would this affect his chances for FP2 massively, but it also really hurts his chances for any potential content later on, including the next title in the franchise. Having been part of a support fandom who has gone quiet before and seeing many other go quiet for a time, it really can hurt your chances, since it's likely that developers will think they have done enough because you stopped pushing the character. This is especially bad though because not only have they stopped supporting Tails, but they are supporting other characters, so now THOSE characters are more likely to be viewed and considered...meaning, currently, the Tails fanbase is shooting themselves in the foot and possibly pushing a self-fulfilling prophecy.
Want: Minor Attachment
There was a period in my life where I moved from one side of the family to the other and they deemed video games as bad for me. During this time I was able to find an old Sega Genesis and buy old games for it from our local Salvation Army every now and again. While I remember Eternal Champions most fondly, this was where I got to play Sonic 2 with my step-sister, which whom we barely ever got along. While I always thought Sonic was cool and I ended up playing many games in the series over multiple consoles, Sonic came into my life when I was starting to become more of a PC gamer and was pushing out my Nintendo roots for a bit, so the series kinda got overlooked outside of my disc for Sonic & Knuckles that I played on PC. I only ever really cared for the first three main characters and Dr. Robotnik, and everything after that seemed dumb to me at the time, and between that and the Sonic fandom itself being what it is even to this day...I never got into the series like many others.
It would be cool to see Tails get in after all this time, but I'm not super attached to Sega of the games they make and haven't been for a long time, and Persona getting in is the one thing that has brought me back to Sega because it's such a cool series that I never knew much about until Smash.
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I withhold any commentary about Danganronpa as a whole since I known nothing about the series and likely will never care to.
by that logic why would any mii costume matter?
They really don't, honestly. The mindset that other non-character content makes a character unable to happen has already seen so much evidence against it that it's kinda crazy, but people will hold onto things now no matter how wrong they are just so that they don't have to accept being wrong. It's the world we live in now.
This particular argument you are having is already over on your opponent's side because Sakurai himself said it was system and engine limitations. Thus, it has nothing to do with Rex's costume at all, and nothing about it's situation has anything to do with they character choice for inclusion or design decisions for them. In fact, it's more of a sign that Sakurai and Nintendo are fixing the mistakes they made by forcing the 2018 release date, making sure to include a character that had a decent amount of request at the time while also making much more profit off of DLC.
In other words, the costume was made because there was a point in time before DLC was going to be made for the game and Sakurai wanted to give XBC2 fans something outside of just Spirits and music. Once DLC happened, XBC2 was made a priority as well as ARMS for a mixture of reasons.
All this confirms is the one thing we already know: that brand-new Mii costumes tend to be for characters that were not realizable at the time, but so long as content continues to be made they don't shut out a character entirely, and that while this has been consistent it isn't absolute.