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My favorite times was gen 5.
>random match making finally built in the games
>no need to buy spin offs and home consoles to have everything
>random ass meta
>perfect blend of 2D and 3D
Gen 3 was really cool for single player (hell, just XD and Emerald would get you more play time than any other gen) and there's a lot of things that I liked in it, but my enjoyment really peaked at gen 5, both because of improvements and because of my own maturity