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B/W's early gyms are memorable to me because they both offer easy counterplay but if the player opts out of that they become very difficult. I realize these are just my autistic rules and you can overlevel/use obviously good pokemon against these trainers.
If you don't use the monkey against the Striation Trio you're forced to handle the monkey with either Lillipup or Patrat, assuming you didn't overgrind. With setup + Potions they're guaranteed to at least get one Work Up for free which could be devastating. Patrat is basically a worse Lillipup but with gimmicks like Bide that could risk free setup.
Lenora also poses a unique challenge because you're basically forced to let something take a potential crit 140 BP normal move. The only thing that can reliably do this is Roggenrola, though ironically you could use your own Watchog with Detect. It also introduces one of the most devastating game mechanics in sleep which could mess up unprepared teams. Cheren gives you Chesto berries before the match which is handholdy but if you don't use them you might end up struggling a lot.
Burgh is easy but credit where its due for having Dwebble. Leavanny could be challenging if the player opted out of a Fire/Flying type.
Elesa's interesting because Volt Switch spam is really annoying. The obvious counterplay is a ground type, but she has two flying types. The fact that both Drilbur and Sandile under level limits barely miss out on useful moves (Rock Slide/Crunch) almost feels like intentional game design. Palpitoad fares a little better but they all struggle to take repeated Aerial Ace spam. Incidentally, once again if you have your own Zebstrika it does really well. Incidentally she also hits all 3 starters super effectively.
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