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I just finished a marathon of the entire series.
In the process I have came to some conclusions.
Gen 1, Nostalgic, but inferior to it's legacy.
Gen 2, Crystal's better then Gold, and Soul is better then Crystal. Kanto isn't as impressive as it was when I was a kid.
Gen 3, great music, great character designs, great post game. Emerald is the undebatable definitive Hoenn experience. ORAS somehow managed to be a shittier version of the games it was "remaking".
Gen 4, I enjoyed the environments, but I kept getting confused on what to do next to progress the plot, it's the only game in the series to have this problem. Platinum's post game is better then the main game of D/P.
Gen 5, I originally dropped the series at this generation, it's a shame I did. I actually have a lot to say about my gen 5 virginity. Excluding N, Black and White have the best main game. The gym leaders all have a important part to play in their respective community's, and they actually fight the main bad guy. Bianca's a better character then everyone of those "rivals" in gen 6 and 7, and you're "friends" have character progression that doesn't have them smile while you kick them around, they actually learn stuff about themselves through the battles. Bianca realizes she's more into learning and studying Pokemon rather then battling, so she becomes the Professor's aid.
Cheren realizes he loves battling strong trainers and watching his Pokemon grow from it, so he became a gym leader.
B2W2 ruined that shit, the story in that game was back to the cliche status quo. The gym leaders do fuck all, and you're "rival"/"friend" is a dumb one note cunt.
The new characters are cool, and the PWT is the best Battle Tower in the series. There's a lot of super cool features I missed out on, but that's my fault. B2W2 are also the hardest games in the series, especially post game.
Gen 6, I enjoyed it quite a bit. The aesthetic of the game is far better on the eyes then Gen 7's everything is a Beach.
Gen 7, series low.