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Attempt two under way.
For some reason when I randomized types and movesets last time, boss teams wouldn't update. Literally every ordinary trainer had updated moves, but Gyms/Rival would keep their vanilla move pool. So I've randomized trainer teams too now, predictably bosses are much harder now.
Brock had a Sudowoodo, not sure what type (either Bug or Grass I believe, it took a SE sun-boosted Flame Wheel easily though) , that was fucking my shit up. Lost Flameo and Ledybot just to take it down.