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Kanto? It's the weakest of them all, but they paved the way for further generations. It was the beginning of many mistakes, but you can't make perfection in your first step.
Johto? It was a bit better, but they peaked their craft in Crystal. Crystal was every previous mistake GF has made, made into the ultimate GBC Pokémon experience. It is a classic and one of my favorites.
Hoenn region? It was the more experimental successor to the first two generations, moving over to a more sophisticated handheld system. They took many new approaches and risks, and I commend them for that. And it's a fun game to boot.
Sinnoh? A bit slow-paced, I must say, but nostalgia clouds my opinion. That being said, traversing Mt. Coronet and making my way to the peak in the back of my family's car as a kid as we came back from road trips at 12 AM in the morning is a cherished memory I will keep for the rest of my days.
Unova? They definitely took a lot of risks there that didn't end well, namely their Pokémon designs, but that's not to say they didn't make some of the most iconic mons to date. And this is where they really upped their lore and plot. It was also a unique middle-ground for 2D-3D map designs; much more beautifully integrated than X and Y, I must say.
Kalos? I guess it is natural for the series to migrate over to 3D maps, and they did a serviceable job, but there were some fallacies here and there. The story was also severely lacking, but I adored the international system. I still look back to my nip friends and wonder how they're doing now. This was also the only generation where you could have one Pokémon from all 6 generations in your party, and that is something special?
Alola? It holds your hand a bit like X and Y, but the character and mon designs are quite interesting, and I appreciate them taking the risk of removing gyms and trying out a new formula. It shows that GF is not as afraid of stepping out of their comfort zones as we assumed.
Galar? LOOOOOOOOOOOOL