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You guys inspired me to run through Crystal with my absolute favorite mon. Sorry for not updating along the way, but it turns out that with turbo and not needing to grind you can blast through in about 4 hours. Started fucking up on taking screenshots at the elite four and never really recovered in Kanto but here's the gist of the journey.
Bugsy was by far the biggest roadblock. Falkner was, surprisingly, super easy. Sprout Tower gave me more trouble than he did. I made the mistake of forgetting my only non-grass move before Bugsy. Took about 20 tries until RNG was on my side. Whitney never bothered to use attract so she went down easy. Morty was the only other major challenge of the run. Took him down with good ol sleep abuse. That was about it for challenges. Elite 4 was tough but still only took one try. Nothing in Kanto stood a chance. Red managed to take our spaghetti hero down once but round 2 was easily secured. Did the league again because im dumb. Tangela is best mon.