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The Sinnoh trio. That's the only trio where I like literally all 9 base, middle and final stages. It’s the only region where I have active difficulty in choosing my starter. Sinnoh, by far. They’re the best starters to ever grace the franchise.
I think I'd have to go with the Kalos trio. It's ironic, since none of them are my favorites of any type. However, there's a thematic cohesion among them that I think is something no other generation pulls off.
I'm going to say Kanto because I like all three final evolutions of the Kanto Starters, with Charizard being one of my favorite Pokémon in the franchise, along with me liking both Venusaur and Blastoise a lot, too. A part of it is nostalgia, but looking back at the starters from other generations, the only other generation where I like the final evolution of all three starters is Gen 3 with Hoenn, with Sceptile being among one of my favorites as well. All the others have some Pokémon that I may really like a lot, such as Serperior from Unova or Greninja from Kalos, but they also have Pokémon that I am either merely lukewarm towards or I actually don't like all that much. With Kanto and Hoenn, though, that's not the case, and what puts Kanto over the top for me is the fact that Charizard is, indeed, one of my favorite Pokémon in the entire franchise.
For me, it's the Unova trio. Even their middle stages seem rather logical, and they're usually the oddball part of the lines. Plus, all three final forms are really great in terms of design, they have the same BST, so it's not like one is technically "stronger" than the others, and they have an interesting dynamic with each other.
Second place goes to Hoenn, as all three are pretty good, though the Mudkip line I'm more meh-ish toward (and it's NOT because of the meme). But all three lines still hold a lot of power and have very good designs. Plus Hoenn is one of my favorite regions.
Third goes to Alola, as all three are pretty solid throughout their evolutions, have great moves and type combos, and generally have pretty good designs. Their biggest downside, however, is their very lackluster Speed, especially in cases like Incineroar, who, despite being my favorite of the three, actually loses Speed upon evolving. So, that drags them down a fair bit. Plus, despite being the starters of their region, they all seem to have some issues with being actually useful in said region, which is another con.
If you want to know what last place is for me, it's the Johto starters. Their designs are just so... bland, their usefulness is very limited, they have such boring types (being mono-typed), and are overall just kinda meh-ish.
Johto and Kanto are the two where I can safely say I like all nine starters (11 if you count Pikachu and Eevee in the latter). Johto has a particularly special place in my heart because they were my first “new starters”. I still remember the feels seeing them for the first time in Nintendo Power and Beckett Pokémon Collector.
But like BigBadButterfree said, Kalos gets a special mention because of the “thematic cohesion” between all three. For how unique Pokémon is, it’s still an RPG series and to see those classic RPG tropes accentuated in the final forms (Knight, Wizard, Ninja) is really cool. And Chesnaught is probably one of my favorite starter Pokémon of all time. If only Quilladin wasn’t a thing, but I even don’t hate it as much as most people do.
In terms of the final stages, Hoenn starters most certainly, as all three are great. However the first stages of the Sinnoh starters will always hold a special place in my heart; I'm just not the biggest fan of Infernape. I guess Unova starters would be third, followed by Kalos, Johto, Kanto, and Alola.
Either the Kanto set (hard to beat the classics on this one; sure, them being the first is part of the reason why they're so iconic, but I think there's a little more to it than that in this instance) or the Kalos set (I think their designs are a little more well-rounded and, like BigBadButterfree said, cohesive among themselves as well as with the European setting, plus their typings are on the more interesting side. Based Delphox being the one Fire/Psychic in the modern sea of Fire/melee...)
Sinnoh ones are my favourite. They all three look great and are pretty good competively.
Hoenn is close second. I also like all three of them.
Kalos third. I love Greninja and Chesnaught probably is my favourite fully evolved Grass starter.
Alola is fourth place. I dislike all three's design on their base stage but their evolution make up for it. Also another trio of all new type combination for starters.
Kanto are alright. Charizard is overrated, both design wise and especially competive wise. Blastoise looks quite decent but is boring to play. Venusaur is my favourite out of them and is actually a quite good Grass starter.
Johto was meh. I like the designs of all three of them in both base stage as well as final stage. My problem with them is, that they are all three mono type and except for Gen 4 Feraligatr, all have rather lackluster movesets.
Unova is last place. Grass and Water mono type + the third Fire/Fighting starter in a row was a bad idea. I also dislike Samurott's and Emboar's designs and wasted potential. Would've liked Water/Fighting and a fast Fire/Ground way more. Serperior's design is quite good, but movepool is lacking and competively the only saving grace is it's ability. It should've been Grass/Steel. All three are so dissappointing.
Gen 1: I can't dislike the OG. They weren't the first gen I played, but the first I watched on the television. I think their simple designs and pretty gradual yet distinct evolutions made them all the more charming. I quite liked the simplicity.
Gen 2: They're okay. Not a huge fan of Chikorita, nor am I of anything beyond Totodile. Admittedly, Feraligatr's design scared me as a child. Now, I think they're just middle of the barrel. Although, HGSS helped improve my image of them.
Gen 3: I really liked how it evolved from cute to tough. Gen 3 is one of my favourites, so I liked this one a lot.
Gen 4: My absolutely favourite, since I basically played DPP at least thrice each. I really liked how each of them sort of looked different from the other and had differentiating auras.
Gen 5: I did not play a lot of BW or B2W2. Although, I do find their designs super cute. Not a very huge fan of their evolutions though.
Gen 6: I really only like Fennekin.
Gen 7: One of my more favourite ones. I find each of them super personable and adorable looking in their own way, although I find their middle evolutions to be some of the less desirable ones.