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SmokedHostage said:
I'd go FireRed or LeafGreen > HeartGold or SoulSilver > OmegaRuby AlphaSapphire > Platinum > Black or White > Black 2 or White 2 > X/Y just to be able to get a feel for all 6 generations.

FireRed and LeafGreen would be a good choice.

Still getting to play the originals with great updates and looks.