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The only hard gym leader if you have decent team building skills is Whitney because of Miltank + you have to go out of your way to get a fighting-type at that point, and even then that Pokemon could get fucked over if Clefairy gets lucky with Metronome.
>mfw Clefairy got Flamethrower and OHKO'd Heracross one time
Though I do admit to getting fucked over by Jasmine in my last playthrough of Gen 2, but that was because I didn't have a ground-type, I had a "no healing items in battle" rule, and my Growlithe was too weak to kill Steelix after dealing with her Magnemite. I ended up putting the Rain Dance TM on Chinchou so it would have enough power to OHKO the Steelix. Good times.