Glad the Mr. Mime question got the ball rolling! I just have one more for the time being regarding your favorite Vileplume. With Alola forms in mind, if you could pick any region where Oddish’s evolutionary family had a regional variation, which region would it be, and what would make the Oddishes, Glooms, Vileplumes, and Bellossoms different there?
Yeah I think when I moved to WordPress people… forgot(?) for a while, I guess, that they could do this? So thanks for that! Anyway, Vileplume. I wasn’t sure how to begin going about this, but I did some reading and learned about a property of the Rafflesia genus of flowers (which Vileplume is based on) that I hadn’t previously known about. We’ve always known that Rafflesia are parasitic; they grow on liana vines and extract water and nutrients from them to sustain their own growth. But according to recent research, they can actually steal genes from those vines, probably to better “camouflage” themselves against the host plant’s immune responses. You expect that kind of thing from bacteria, but in a parasitic plant, it’s really weird and interesting. The baseline Kanto-morph Vileplume doesn’t lean into the parasitism angle very much; the Rafflesia is a source for her physical appearance, and for Gloom’s notorious stench, but not their behaviour. They learn the Grass-type draining attacks, Absorb, Mega Drain and Giga Drain, but that’s about it. So let’s have Oddish, Gloom and Vileplume that parasitise other Grass Pokémon and have taken on a couple of their characteristics via horizontal gene exchange. Ideally that would include Tangela or Tangrowth, since real Rafflesia are vine parasites, but unfortunately there is currently no region in which Oddish or Gloom coexist with them in a single route. Hmm… where do Oddish and Gloom coexist with a significantly larger Grass Pokémon…? Ah – central Hoenn, with Tropius. I would expect Oddish, Gloom and Vileplume variants that parasitised Tropius to have brown skin, to match their hosts, and longer roots with more branching, to anchor themselves in the host’s skin. They could plausibly be Grass/Dark or even Grass/Bug for the parasitism theme, but I’m not sure how to change the physical design to fit that in a way that makes any sense. If we run with the gene transfer idea and have Gloom exploiting Tropius for genetic material and not just nutrients, we could have Vileplume eventually begin producing fruit similar to Tropius’ bananas (maybe containing seeds that can be carried long distances by other Pokémon), and Bellossom pick up leafy fairy wings and switch type to Grass/Flying. Let’s call that a start.
Pokémaniacal 
Ever the academic, aintcha? 😛 If you don’t mind, Imma chime in here and go the opposite route of emphasizing Oddish’s mandrake elements, and additionally the role of plants in witchcraft. I would have Oddish be a pure Grass-type, then evolve it into a pure Grass Gloom with some minor Poison powers. This Gloom has smaller leaves but a bigger body with a more root-based design. Its saliva (to tie it with the bits about Kantonian Gloom’s sweet saliva) can be brewed to make drinks with hallucinogenic properties, which makes it popular among certain people bold enough to try. Some people even believe it might give you magical powers if you brew it under a full moon’s light (another tie back to Kantonian Gloom).
Level it up with high friendship in the night turns it into Grass/Dark Vileplume who fights with ungodly sonic attacks in the night, not unlike Noivern. Its loud cries echoing through underground tunnels dug by Onix or Excadrill led to legends of subterranean people before it was identified as a Pokémon. It’s a blasty tank with high special stats, Snarl, Hyper Voice, Boomburst, and maybe a Liquid Voice-like signature Ability that turns its sound moves into Dark attacks, and maybe boost their power by 20%. Perhaps we can even get away with giving it Earth Power, to deal with all those pesky Fire- and Poison-types? Level it up with high friendship in the day turns it into Grass/Fairy Bellossom, who focuses more on potion-making. Old lore would have you believe that if you trained one, you would mysteriously be more attractive to the object of your affections (a PG version of Alraune’s supposed effects on your sexual prowess). It’s a special wall of a support Pokémon with Life Dew, Aromatherapy, Flower Shield, and maybe a signature Ability that does something like, when it consumes its held Berry, it applies the effect to its entire side in Doubles/Triples (so e.g. a Sitrus Berry would heal both it and its partner). As a bonus, the Ability makes Bellossom immune to the poison status. Maintains and makes explicit that nice sun-and-moon duality between Vileplume and Bellossom, which is always a good thing. And of course, these Pokémon are found in Glimwood Tangle in Galar, right next to the fae settlement of Ballonlea.
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