Wartortle: Now knowing Blastoise wasn't the original final evo but rather a completely different Pokemon which took the place of a more bigger turtle-like kappa Wartortle, it's hard to see the family the same way I once did. Before I just assumed they wanted to give Wartortle its own identity from Blastoise like the other Starters had to their final evos, though I guess that could be one of the reasons why they combined the families together. I do like Blastoise more than the more kappa-like Wartortle, though it does make Wartortle a bit of a sore thumb and in restrospect not that great of a transitional stage. Would like for them to explain why it loses the longevity fur and where the cannons came from, like does it offer up longevity in exchange for a mutation that'll give it greater power?
Croconaw: Now the Johto Mid Stage Starters aren't all that odd (though Chikorita's almost was). However there is one thing about Croconaw I never got: why does it body pattern change to resemble an animal-skin cloth that caveman stereotypical wear? The family has nothing to do with caveman or anything prehistoric (aside crocodiles being a very old species that haven't changed much for millions of years), Totodile and Feraligatr lacking the pattern. And all its dex entries are about its biting prowess. Also the animal-skin clothes were often based on big jungle cats, rarely crocodiles.
Combusken: Yes, yes, it's a c*ck that looks like a c*ck, HA HA HA. Juvenile humor aside, you can SORTA see how certain elements of Combusken can transition to Blaziken, but there's still certain questions that doesn't make it as obvious as its fellow Hoenn Starters. For me it's mainly the legs, it goes from bald to covered in a long pants-like down. And while I can see how the top part of it becomes Blaziken's crest, the beak/face transformation is a bit of a jump.
Prinplup: As
greentyphlosion has noted, the problem with Prinplup is that it doesn't stand out enough from Piplup nor really help with its transition to Empoleon. Sure it started with the crest (though it doesn't look like anything, let alone a trident) though Empoleon's most notable feature, it's steel wings, have no hint of being developed aside Dex descriptions saying Prinplup's wings can cut through tree branches. I think they should have added some
epaulette looking decorations to its shoulders. Not only would they eventually hint toward Empoleon's steel wings, but Napoleon Bonaparte which the Piplup family takes inspiration is often painted wearing epaulettes.
Pignite: It's not that Pignite is a bad transitional Pokemon, its actually pretty good at that, this time its Pignite being an evolution of Tepig. Tepig is a pretty simple Pokemon, it's a piglet. And then when it evolves it suddenly becomes bipedal, gains a lot of weight, and becomes a (mud) wrestler with fancy golden overall buckles. It went from simple animal inspiration to multiple complex concept inspirations. Now it's not that bad but still a sudden shift that could catch you off guard if you weren't expecting it.
Quilladin: I think the problem with Quilladin are the eyes. I just did a quick Paint where I colored in the white of the eyes with the color of its skin and it looked SO much better. I know its round armor caught a lot of people off guard when they first saw the stock art but when it's moving it doesn't look that awkward. It's just the eyes. And I get why the eyes are like that, to transition into Chesnaught which has whites around its eyes, but Chesnaught's face also completely changes shape while Quilladin still has Chespin's face which was made to have beady eyes.
Brionne: Poor Brionne, I remember many's complaint about it: "It's just a Popplio in a tutu". And we weren't wrong, but also aren't completely right as there's other new details like the white bubbles on the ears, white tail markings, and eyes looked more feminine. It looking more feminine overall was the important transitional detail, though it's also still a leap away from Primarina so a little more Primarina and less Popplio aspects might have helped it (and make Primarina not so much a major change).
Thwackey: The onsie should have been made into a hooded shirt. Thwackey looks like an awkward Grookey and in no way transitions into Rillaboom.
Drizzile: Now I like Drizzile just because it's so blatant an "angsty teen" Pokemon. Sure the Sobble family don't really transition between stages that well, but at the same time you could create a small narrative: starts as a shy child that easily gets upset, it then becomes an angsty teen that wants to be left alone. No doubt teased, it swears that while everyone else lives out their lives pushing papers it's going to become an international spy. And so it did.
