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As expected, Kirie just destroyed Blaine and Giovanni. After that I pretty much just spent an entire day grinding. The E4 were easy, most of them getting swept by a single Pokémon. Blue went okay, other than his Cloyster almost killed my Pikachu, Ziggy, with a 5-hit Spike Cannon. All in all, pretty easy (thou having to grind to make it easy kind of invalidates that, maybe).
I am immensely glad to be done with Gen 1. Red was a blast, but Blue was a slog and Yellow was only made bearable due to the randomizer forcing me into many routes with no valid Pokémon to catch. I haven't played Gen 2 since 2003 or so, but I remember it being much less awkward - hopefully that holds true.
Now - to Gold.