>>51095890I mean with Gen II even so they really shouldn't have had both Chuck and Bruno, one specialist who would've been able to use both Heracross and Hitmontop would've worked well and maybe have the other be something else. You also have stuff like Jasmine using two Magnemites or Morty not using a Misdreavus and just the general lack of Gen II Pokemon where the option is present and would've fit the character.
Gen III and IV though yeah, definitely a case of were they just not thinking at all, like Gen I gave us Seel and Shellder, both of which would've fit well enough in the oceanic Routes (Shellder via dive akin to Clamperl) and both evolve into part Ice-Types. If you wanted to ensure variety you could have Jynx in Shoal Cave and maybe Sneasel on Mt. Pyre just for some location variety. For Ghost-Types admittedly you're still kinda stuck with the then five fully evolved in Gengar, Misdreavus, Dusclops, Sableye & Banette and Misdreavus would probably end up on Mt. Pyre but you could have Gastly around Mt. Chimney akin to Koffing and Grimer given it's meant to be a noxious gas Pokemon.
For Gen IV I mean they kind of address it in Platinum but Fuego Ironworks seems like such an obvious place to work with or hell even Iron Island for Pokemon like Slugma and Magmar. Admittedly I think given Flint's character the most fitting would be; Houndoom, Flareon, Arcanine, Infernape & Magmortar although the only place I can think that would be really fitting for Growlithe would be the Trophy Garden.
