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I wouldn’t recommend either version of gen 2, actually. They can be incredibly unforgiving if you don’t know what you’re doing, to the point where you can fight every trainer you meet and still be a good 10-20 levels behind by the time you get to the last gym. If you want an older title, gen 3...

Any game from platinum to Black/white 2 is your best bet, as the first few gens are horribly outdated, and the later entries can be hell to get into due to their hand-holdyness. Any of the games from gen 3 (ruby, sapphire, emerald, fire red, leaf green) are also good entry points. Just as long...