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1. Prequel to RSE.
There are plenty of games that release the prequel much later than the first game, so wynaut RSE? We can have the protagonist be the initial helper of Birch, and travel around collecting badges.
5 to 10 years before the setting of RSE...
Rival: Steven Stone
Villains: Team Weather (Originally, there was one team that wanted to control the weather, but they eventually split into two - Aqua and Magma)
Gym Leaders and Elite Four
Roxanne's Dad/Mentor
Brawly's Mentor
Wattson
Someone who's a Fire-type Specialist
Someone who's a Normal-type Specialist
Winona's Mom/Mentor
Tate and Liza's Parents
Juan
Flannery's Grandfather (possible Ground-type Specialist)
Drake
Glacia (something like a teen prodigy)
Someone Specializing in whatever type that wasn't used.
A Champion specializing in Diversity or whatever type they want.
I don't think I like the idea of prequels for Pokemon because there's not much to go on for the regions' pasts and it wouldn't make much sense because the storyline would probably end up contradicting the originals. Just about the only prequel idea I can see working is if they did one for Black and White based on the two brothers in the Unova legend.
3. Sequels of RSE
5 to 10 years later from the plot of RSE, another trouble occurs. A new protagonist starts their journey. Depending on the gender, the initial protagonists are living differently. If the protagonist is a boy, Brendan is the 'Red' in the remake, while May works at the Weather Institute - and vice versa if the protagonist is a girl.
I don't think the older characters' roles should depend on your current character's gender, but if they don't do that, it presents an interesting problem. If the sequels aren't compatible with the originals, how will the character roles be determined? You can't use Memory Link like you would with BW1 -> BW2. I think it might be best in this case to just give them vague references and have them not show up.
Rival: Wally
This would be quite sad, after 5-10 years he becomes the rival to a completely new trainer who would end up completely owning him in every battle. No, I think they'll use a new rival. Wally would probably have a different role in the sequel and be a more experienced trainer, much like Cheren and Bianca in BW2. Maybe he could even be Champion, now wouldn't that be a neat twist?
Gym Leaders and Elite Four
Norman
Wattson's Apprentice
Brawly
Roxanne
Flannery
Tate and Liza
Phoebe
Wallace
I'm not understanding the storyline path here. Also, why would Phoebe step down from Elite 4 to gym leader?
FireRed and LeafGreen would get stale if they re-remade them (unless they made sequels) and Kanto is still playable through HGSS (albeit a bit nerfed, but there aren't really any glaring problems with Kanto in the remakes). As for 4th gen onwards, it's not hard to get them at this point and any existing DS/3DS model can play them, so they're far from obsolete.
Or a ds lite. And if they remake Ruby and Sapphire because of that, doesn't that mean they should remake Firered and Leafgreen too? Oh, and they might as well remake Diamond and Pearl because they weren't pretty enough and and DS games look weird on the 3DS. And Heartgold. And Black and White. And X and Y. (I don't like remakes ok)
FireRed and LeafGreen would get stale if they re-remade them (unless they made sequels) and Kanto is still playable through HGSS (albeit a bit nerfed, but there aren't really any glaring problems with Kanto in the remakes). As for 4th gen onwards, it's not hard to get them at this point and any existing DS/3DS model can play them, so they're far from obsolete.
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