I think I'm going to update my ideal roster:
No cuts from Smash Bros. 4, including DLC characters. However, ideally, Ganondorf, Lucina, and Dark Pit would be de-cloned in the transition (Dark Pit and Lucina to make them more unique as characters, Ganondorf to make him closer to how he is represented in his series).
RETURNING CHARACTERS:
Ice Climbers: I'm not a huge fan of entire series being removed from Smash Bros.; I feel like that sets an unfortunate precedent. Besides, even though I almost never played as the Ice Climbers, they were completely unique characters, their removal caused a lot of outcry, and they have awesome victory music - I can't justify leaving them out.
Snake: there's a lot of overlap with the Ice Climbers in terms of my reasoning - plus, personally, I found him fun to play as, and no character in the current game has a similar playstyle, though that's just a side note. Given that this franchise is a crossover between dozens of series that are completely different, in terms of gameplay and tone, I never understood the argument that Snake "didn't fit" in Super Smash Bros. when we can have Marth tossing blue shells from Mario Kart at Kirby while fighting on a space ship.
Wolf: while I disliked Wolf's inclusion when Brawl was first released, he's grown on me; at first, I thought he was a Fox clone, but that's only in an extremely superficial sense. (only his B moves are vaguely similar, and his final smash is near identical) Just change his final smash to something that actually suits the character (calling in Leon and Panther to blast the area in their Wolfens, for example) and there'd be no problem.
Squirtle: while Squirtle tended to get overlooked given that Charizard was an option, he had a completely unique moveset and would work fine on his own. Just get rid of the type advantage system (which only seemed to benefit Charizard anyway, given the lack of water and grass based attacks) and the stamina mechanic.
Ivysaur: see Squirtle.
NEW CHARACTERS - RETURNING SERIES
Captain Toad: aside from characters who I have later on this list, Toad is one of the biggest Nintendo all-stars who is missing from the Smash Bros. roster. Toad has been playable in Mario games since nearly the beginning, and with Captain Toad: Treasure Tracker giving him a lot of consistent material to work with, I feel like now would be the perfect time to add him.
Dixie Kong: with Tropical Freeze coming out half a year before Smash Bros. and the utter lack of Donkey Kong content in the final game otherwise, I'm honestly surprised that Dixie didn't make the cut. Starring in two of the three Donkey Kong Country games, Dixie's only behind DK, Diddy, and maybe K. Rool in terms of importance to the series, and with Tropical Freeze expanding her options even further, there's quite a bit to work with.
King K. Rool: seeing as Donkey Kong has undergone a major rebirth since Donkey Kong Country Returns, I feel like two new characters can be justified. K. Rool may not have been present since that time, but that's done nothing to diminish his popularity - the question faced by every new Donkey Kong game is "where are the Kremlings?", and despite the Mii costume, his fanbase remains as dedicated as ever. There's tons of potential for moves, as evidenced by his wildly different boss fights over the course of the three DKC games and Donkey Kong 64 alone, and he's easily the most iconic villain of the Donkey Kong franchise. (who remembers the names of the final bosses of Donkey Kong Country Returns and Tropical Freeze without having to look them up? Exactly)
Midna: I realize that there haven't been many major Zelda releases since Melee (it's just been Wind Waker, Twilight Princess, and Skyward Sword, at least as far as home console games go), but that's no reason why Zelda's presence on the Smash Bros. roster should be basically unchanged since 2001. Zelda's introduced quite a few new characters that have gotten a significant fanbase, none moreso (at least, if having two playable forms in Hyrule Warriors is any indication) than Midna. I could have gone with Impa or Ghirahim, but of the three, I feel like Midna's the more noteworthy of the three.
Grovyle: I considered Genesect for this spot, or leaving it blank for a popular Pokemon from the next generation, but I feel like Grovyle would work well for Smash Bros. The third generation of Pokemon really got skipped over in SSB, seeing as focus went from Gen. 2 in Melee to Gen. 4 in Brawl, and Grovyle is (at least, by my understanding - I haven't played the games in question) one of the most important characters in the Pokemon Mystery Dungeon games, so he could work as a representative of that sub-series. Pretty much any Pokemon could go here, but I feel like Grovyle is a nice fit, and it seems like he would work better as a playable character than Sceptile, at least from a design perspective.
Bandana Waddle Dee: in recent years, the spear-wielding Waddle Dee has become a pretty major character in the Kirby games, being a playable option in Kirby and the Rainbow Curse when even Dedede and Meta Knight were left out. Based on Return to Dreamland alone, there are a lot of options for this Waddle Dee's moves, and it seems like he would play quite differently from other characters based on that.
Ridley: let's be honest - Metroid has really gotten the short end of the stick when it comes to franchises on the Smash Bros. roster. Even Donkey Kong has two distinct characters - Metroid, for all that it's grown in size and popularity over the years, has two different versions of Samus. Ridley's easily the most prominent villain in the franchise, seeing as he's responsible for the death of her parents and appears in almost every game in the franchise as one of the last boss battles, and his size isn't as big of an issue as some people believe. Over the course of one game, Ridley's size changed significantly (in Metroid Prime 3, where he shrunk down to about a third of his initial size between boss battles), and it's not like the proportions of characters haven't been wildly adjusted to make them work in Smash Bros. before. (take Palutena for example, who goes from twice Pit's height in normal circumstances to shorter than Pit in Smash Bros.)
NEW CHARACTERS - NEW SERIES
Sukapon (Series: Joy Mech Fight): admittedly, this character kind of comes out of nowhere, seeing as he's from a one-off Japanese exclusive NES game where the plot is almost identical to Mega Man, but Joy Mech Fight was one of Nintendo's first and only attempts at a traditional fighting game, so I think it would be nice to reference that often forgotten part of Nintendo's history in Smash Bros.
Mike Jones (Series: Star Tropics): the Star Tropics games were a pair of NES titles which were never released in Japan, so his inclusion seems less likely than a character from that era who was exclusive to Japan, but I found it weird that Star Tropics wasn't even referenced in any Smash Bros. game, not even with a sticker. I only got into the series a few years ago, but I found it to be an interesting blend between Zelda and the Mother series, and even though Mike has some similarities with Ness, the sheer variety of weapons found in the Star Tropics games would result in the two playing quite differently.
Isa Jo (Series: Sin & Punishment): it's a tough choice between Isa and Saki, but Isa won out due to his jetpack and greater maneuverability. The Sin & Punishment series has gotten a lot of exposure since its release on the Wii's Virtual Console, with a sequel being released worldwide and both games being released on the eShop recently. Of all of the assist trophies in Brawl, Saki's seemed to act the most like a playable character, with lots of movement and a variety of attacks, so I feel like the inclusion of a character from that series definitely seems like an interesting possibility.
Ray (Series: Custom Robo): I'm not entirely sure why all Custom Robo content was removed from Smash Bros., but given the large number of weapon types and mobility options, I could easily see Ray working as a playable character. The Custom Robo series may not be the largest Nintendo series, but it's certainly not the most obscure, with about half a dozen games being released. I feel like, when it comes to new series, Smash Bros. tends to focus on really old or really new, with the stuff that falls between getting thrown to the wayside; that's one thing that I'd really like to see change.
Isaac (Series: Golden Sun): similar reasoning to Ray, though at least Golden Sun got some stage music. I know some people think that Isaac would be just another swordsman, but I've barely even played Golden Sun and I know for a fact that's not true. Between the summons, earth- and plant-based spells, and yes, his swordsmanship, there's a lot of potential variety there - he'd be much closer to Robin (though with completely different magic abilities) than Marth.
Inkling (Series: Splatoon): I figure they're a given for Smash 5, seeing as each game tends to focus on the previous console generation as far as the rosters go and Splatoon is clearly a big hit. Don't think I need to elaborate too much; they're popular, have lots to work with, and characters like Mega Man show that projectile-heavy characters can work in Smash Bros.
Wonder Red (Series: The Wonderful 101): this seems less likely than Inklings, given that the game didn't do well in terms of sales, but given the sheer amount of Wonderful 101 representation in Smash Bros. already (at least, compared to how well it did), it seems possible. I don't know whether Wonder Red could just use Unite Hand for his moves or if he'd have to use other Unite Morphs like Sword or Whip (haven't gotten very far in the game, so I'm not sure what other upgrades there are), but either way, there's a lot of options there, and an inclusion in Smash Bros. would definitely help to give the series more exposure, as seen with the Mother series, Fire Emblem, Kid Icarus, etc.
Rayman (Series: Rayman): now we're getting into third parties. Despite some missteps (ex. releasing Watch Dogs months after the other versions, long after anyone stopped caring about it; delaying Rayman Legends days before its release in order to make it multiplatform and release it at the same time as other consoles), Ubisoft has still been one of the biggest supporters of the Wii and Wii U, and Rayman's recent platformers compete with (or even surpass) Mario's in terms of quality. The fake Rayman leak helped with that, and I feel like it got so much mileage because, while it kind of came out of nowhere, it was still believable. That shows me that Rayman's inclusion would be met positively; plus, I found it a waste that they got the rights to use Rayman but only made him and a few supporting characters into trophies.
Bayonetta (Series: Bayonetta): before, I thought this was a pipe dream, but the inclusion of Ryu showed that third party companies can get more than one character, and as far as non-Sonic Sega characters go, Bayonetta's easily their most prominent. Bayonetta 2 was easily one of the biggest third party games for the Wii U, if not any Nintendo console, and she's appeared in Nintendo games and advertising campaigns before, so Sega seems to have no issue with Nintendo using the character. Her appearance in Anarchy Reigns showed that she can be toned down to a level that would work in Smash while still staying true to her character, and the biggest problem doesn't seem to be finding moves to use, but rather, trying to narrow down the moves that she already has.
Shovel Knight (Series: Shovel Knight): Shovel Knight doesn't seem like the most likely of the third party characters; even Bayonetta has multiple critically acclaimed games in the short time that she's been around. However, Shovel Knight's made a huge splash with Nintendo, basically becoming the face of the eShop, and being the only third party character not in Smash Bros. to get an amiibo at this time. The entire concept of Shovel Knight is based around 80s 2D platformers, and given how well 2D platforming characters make the transition to Smash Bros., it seems quite natural to consider him.
Terra Branford (Series: Final Fantasy): Square-Enix and Nintendo were once closely associated, and while I could have gone with a more generic option that encompasses the entire series, like Final Fantasy's Black Mage or Dragon Quest's Slime, I decided to go with Terra Branford from Final Fantasy VI, the last numbered Final Fantasy game on a Nintendo console. She seems to be the main character (though with more than ten characters, all of whom get a lot of focus, it's hard to be sure - arguments could be made for Locke or Celes), and her abilities could work well for showing off the magic system of Final Fantasy, with her Esper form seeming like a natural fit for a Final Smash. Given how long of a history Square and Enix both have with Nintendo consoles, it would be strange to not include one of their characters, and while my choice might not be the most widely considered, Terra's still the Final Fantasy character who I'd most like to see added to Smash Bros.