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It's tough, I like all the gens. I would go with II because I had the most success there. Plus, going back to Kanto and facing Red, who you once were, was chilling and exciting.

Gen I was a great start and my childhood, but realistically, it's broken in some ways (damn those Psychics).
Gen III and VI were solid experiences that provided new worlds and new gameplay experiences to the established gameplay.
Gen V and VI were great as well. Creating new energy for me as an older and more experienced gamer. The new Pokemon, the Megas, the graphical evolutions. You can just tell that V was sorta teasing how mainline Pkmn games could potentially be when the environments get out of their 2D overworlds.