This is one of my favorite pastimes. I always focus on trying to bring in more retro/obscure Nintendo representation, then hit interesting new IPs, and finally 3rd party reps that make sense or are overdue. Also, going to shill real quick for my "Super Smash Sisters" idea I posted a long time ago after being challenged to create a huge all female cast for a Smash game.
The link is right here.
This is my attempt at a Smash 5 roster with very loose limits (32 newcomers, 4 returning vets):
*As a quick note, I'm not going into moveset changes unless I think the moveset change is important to changing the character (or notable). I'm also not going into alternate costumes/alt characters unless they already exist in the game and need to be addressed. I think we can all assume that both of these things will be fleshed out further in the actual game, so I will just briefly comment on what I feel necessary to explain my hypothetical changes. Also, I only limited myself to two 3rd party characters and trying to stick to as unique and varied a selection of Nintendo reps as I could think of while not going extremely overboard more than I already did (because I could have, easily).
Smash 4 Veterans: all characters from Smash 4 return. I'm not a hater. The following changes would have to happen to the veteran cast, however:
- Dark Pit: becomes a premiere costume for Pit, with all the same differences and unique content... just takes him off the CSS, basically
- Dr. Mario: same treatment as Dark Pit, becomes costume for Mario
- Ganondorf: now fights with dual blades as a reference to Hyrule Warriors, with a moveset that doesn't change much except to compensate for his new choice of weapon... his trident comes out during his Final Smash now, but he still turns into Ganon
- Link: becomes his BotW incarnation, but still has the classic moveset with the weapons changing to match BotW weapons
- Lucina: stays her own character, with some moveset changes to make her feel different enough to warrant this
- Mario: loses FLUDD for his Mario Tornado again, now based on his Galaxy and 3D World spin jump... tossing his cap from Odyssey is worked into one or two of his standard attacks... and his Cape now works like it did in Mario World, becoming a full 360 degree spin (and giving him a chance to hover/divebomb opponents)
- Mega Man: his jab gets more range and he becomes the first character who can move and jump around while charging his smash attack... moveset shifts to accommodate more combat focused Master Weapons (mainly, he ditches Metal Blade and Leaf Shield for better options)
- Olimar: Alph diversifies a bit, gaining moveset tweaks including Rock Pikmin, while remaining a costume for Olimar
- Wario: just because it bugs me, he gets back his shoulder charge for his FSmash
- Zelda: doesn't change much, but noted that she's based on her BotW incarnation
Series Veterans: returning characters from 64, Melee, and Brawl
- Ice Climbers: same as they always were, but get a new Final Smash
- Wolf: back and ready to fight
- Pichu: another returning vet, gets some moveset tweaks to make it a little different from Pikachu.. including its own Final Smash
- Snake: because screw you, that's why
Newcomers: all new fighters (retro, new IPs, and 3rd party)
- Toad: speedy, hard hitting, and small, he uses a combination of Mario 2 and Captain Toad abilities (Mario series)
- Dixie Kong: sort of a Luigified Diddy clone, attacks using her DKC:TF and DKC2 abilities + Diddy's (DK series)
- K. Rool: attacks with a mixture of his various gadgets, he's a heavyweight that relies on traps mostly (DK series)
- Captain Syrup: another villain, she's a fast sword fighter with specials revolving around thievery and pirate tech (Wario)
- Impa: based on Hyrule Warriors incarnation, she mixes up Ike's swordplay with Sheik's speed and specials (Zelda)
- Ridley: he's not too big! A massive, speedy fighter with limited flight and insane range, but he's a big target (Metroid)
- Marshadow: a surprise rep from Gen 7, but more clever than a starter. Small, teleporting shadowboxer (Pokemon)
- Krystal: completely unique moveset that relies on her staff and psyonics (Star Fox)
- FE Rep: could it be Lyn? somebody from FE Heroes? FE Fates? I don't know and don't care, but it fits (Fire Emblem)
- Bandana Dee: the only rep left from Kirby... fights with his spear and a mixup of Parasol and Beam abilities (Kirby)
- Inkling: can swap genders, gimmick where they "ink" the stage to give them an ability to swim around easier (Splatoon)
- Spring Man/Ribbon Girl: not sure which to choose... either would have really good range, but limited options (ARMS)
- Lion: a heavyweight who relies on guns and launching himself around the stage to deal damage (Codename: STEAM)
- Lip: fan favorite flower fairy, can "catch" projectiles, poison foes with DOT flowers, and drop garbage blocks (PdP)
- Barbara: bat musician and magician, she attacks with playing cards, her guitar, and sound waves (Jam with the Band)
- Dillon: upgraded from AT, he fights by dashing into foes and slashing them up... combo friendly (Rolling Western)
- Jill: riding the Drill Dozer mech, she is a small heavy weight that fights with various drill attachments (Drill Dozer)
- Sami: mixes up guns, explosives, and strikers to create a playstyle fresher than Snake's (Advance Wars)
- Isaac: a spellsword who rarely uses a sword, relying on psynergy to move foes or summon earthen magic (Golden Sun)
- Elma: a mixup character who can swap between dual guns or dual blades (Xenoblade Chronicles X)
- Rola: an alien princess who fights using MA and some tech, summons her mech suit for stronger attacks (Metal Falcon)
- Sukapon: quirky robot with disjointed limbs (+ hitboxes) who grapples foes and blows up on them (Joy Mech Fight)
- Mike: another jack of all trades who wields various tools to fight: swords, slingshots, a yo-yo, baseballs... (Star Tropics)
- Space Firebird: a "reimagined" classic character, a humanoid and huge space phoenix that fights with a variety of projectiles and summons (Space Firebird)
- Chibi-Robo: can grab anything and "dispose" of it... also has a lot of neat tools to fight with (Chibi Robo)
- Takamaru: samurai with a katana and projectiles, can turn invisible and call lightning too (Riddle of Castle Murasame)
- Starman: a wrestler through and through, who grapples everything (Pro Wrestling)
- Simon Belmont: fights with his Vampire Killer whip and some classic subweapons (Castlevania)
- Bomberman: a trapper who lays bombs around the stage that explode on their own accord, can alter the bomb elements and also lay bombs/move them around a variety of different ways (Bomberman)
Some Assist Trophy Ideas: Because there are just some characters I love too much.
- Ray MKIII: he went missing after Brawl... for shame
- Trixie: the "mascot" of Barker Bill's Trick Shooting, which also featured the Duck Hunt dog...
- Ibis: from Pilotwings, she could fly around the stage dropping hazards
- Beyon: cat monster from Card Hero who uses diamonds to attack
- Moogle: cast spells and dance, basically. why doesn't FF have an assist?
- Hikari & Donbe: they could come out as a pair and use the 3 animals to attack (monkey, dog, pheasant)
- Anything Eternal Darkness: can they even use this?