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Tails is another Sonic character, not his own series. So... that could matter, depending upon how Sakurai views it. He has made notes of representation mattering when it comes to series, but also the fact 3rd parties are guests. So that may or may not be relevant.What are the chances of third party companies getting to double dip? Like Rabbids and rayman or sonic and tails, hell maybe even banjo and Conker etc . Many third party companies have good character choices but I’m wondering if we ever get multiple third party characters from the same some companies......
Of course, Rabbids are basically their own series now, so they have a decent chance of getting in. I'd say they're probably more likely than Rayman, but that's due to the fact Nintendo allowed them with their biggest series as a crossover, with no Rayman in sight and treated as an unrelated series for the purpose of character appearances. This is kind of important and shows how much they trust in the idea of using them, so them getting into Smash would be relatively easy. Sakurai is another factor however, and he may not find them interesting as playable(though Mii Costumes I could see them being otherwise, as they'd fit any style and already have multiple weapon options).
As for the Microsoft options, Conker is nowhere near as big as Banjo & Kazooie(who aren't really that iconic as is, outside of n64 fans), and then you have actual big series like Killer Instinct(which has two potential options, respectively), Halo(with maybe up to 3 notable characters, but Master Chief is the most well known), and Minecraft(with Steve? being the main character and all). I don't think we'd get two Microsoft characters, unless it was a unique package deal, like Jago and Fulgore, who are the big guns of Killer Instinct. Though see up above why I don't think any 3rd party series is likely to get two characters.