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Hmmm... unless I have Geodude, I always have trouble with Miltank, and unless I have Ampharos (with Fire Punch) or Feraligatr I always have trouble with Steelix. I'd say Steelix is a smidge more difficult, if only because fire types get hit hard by Steelix' Rock Throw and Ground types get annihilated by Iron Tail, whereas Miltank's main strategy can be stopped more easily by just using Smokescreen or Thunder Wave.
Anyway, we all know that generally, Clair's Kingdra is the hardest Gym Leader.
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