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I'm back, about a month later, finishing the Gold leg of the run. Nothing that interesting happened in Kanto, and Red wasn't a challenge.
I have something I want to do when I start gen 3 games. I never did a lot of the post-game stuff in most games, especially the battle tower/frontier etc kind of things so I think for the last game of each gen (plus remakes) I'm going to do most post game content, doing all the contests, battle tower/frontier stuff, and complete the pokedexes. I wont nuzlocke these parts though.