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Immortal said:
This is outright awesome, for the record. Please continue exploring these scenarios. They're really interesting and you're clearly thinking them out really well.
I don't have the time to contribute quite at this moment, but before one of you comes up with it, I'm calling dibs on Pokemon not being released for the Gameboy in 1996. Although I'm not sure what exact difference I'm referring to, there are a lot more wide-ranging effects for this than you'd think. Especially with Nintendo's "never made a loss" reputation being singlehandedly supported by Pokemon during the sixth-ish generation and Nintendo's handheld stronghold being so severely weakened without it.

That is pretty Big What if Question, Pokemon in Hindsight is maybe the third best choice have nintendo made in his whole history(the first was jumping into videogame business, the second giving a job to Shigeru Miyamoto even when he admit he would not be sure that he will forever in his job, he need the job as financial security before becoming a mangaka....them he found videogames fun thanks to Space Invanders and the rest is history) but at the moment, that was big gamble and almost like a vanity project between Game Freak(they were making game to both SEGA and Sony Imagesoft, Later computer entretaiment), APE Inc/Creatures(who was using as way to push multimedia plans) and the same Shigeru Miyamoto(who was the main reason Yamauchi approved the project, even Miyamoto fund pokemon with part of his own salary), as a way to push the them ailing gameboy  and maybe becoming another second tier franchise as Fire Emblem or Mother nas his time, them thanks to the social nature of the game, and the secret pokemon(mew) who Satoshi hid in the game, the whole thing explode, and them with the anime approved and Creatures a charte blanque for multimedia rerelease... Pokemon is the second money maker behind only mario.

But at the same time, pokemon is pretty big, with several license for toys(Bandai, Takara-tommy, Hasbro), an Anime who have never stop(except for a incident) since 1998, anual movies, and along etc, but at the end not only paid itself, is almost like Nintendo secret weapon for handleds nowadays.

Without Pokemon, besides the Handled market will be more smaller(A lot smaller even in japan), that will affect how nintendo make handleds, The gameboy color was to be released in 1996 holidays season, but pokemon make that push almost two year thanks to the new demand of the old Gameboy and the game boy advance was delayed a year thanks to the same time(the legendary project Atlantis in the 90's), that will affect somehow his 'imitators'(Digimon was in plan, but pokemon make those to be pushed to ride into the wave and compete, Medabots was based into gundam derivate but pokemon free pubilicty was fine, and monster ranchers who was the direct clone) and the demographic of Handelds(i never want a gameboy before pokemon, heck even if like Mario and Zelda).

I'll tell you something, that is a true game changer what if(like if yamauchi never enter into videogames or  Nintendo and Sony manage to work together), you should add more ideas