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>Gen 1 was my first and my most nostalgic Gen (Also the longest one). Has a shit ton of issues and is honestly next to unplayable now, but still a fave. Yellow was fun, and I wish more of the side games had more of its vibe.
>Gen II has my favorite games in the series, but does have some post game issues with scaling and the lack of anything to do in Kanto. Crystal version was honestly kind of shit, and the worst of the re-releases.
>Gen III is a mixbag. I absolutely hate vanilla RS, but love FRLG (Which fixed a lot of the engine issues RS had and introduced icons for items). Emerald was pretty damn awesome, even if it had some shortcomings here and there. Colosseum and XD were a nice experiment, but each had its own issues (Although I wish they would make another console RPG).
>Gen IV is probably my favorite. I really liked D/P, and Emerald fixed the issues it did have with speed and the Dex (Also had the best spread of Pokemon). HGSS is my absolute favorite of all the Pokemon games and fixed pretty much everything I had a issue with in GS.
>Gen V was a meh generation. I liked that they experimented with a story in BW, but it fell short at times. I honestly do not like Unova's layout, and have mixed opinions on the Pokemon (But do like that they tried to start from square one). BW2 had a worse story, but awesome endgame content. Least favorite gen outside of Gen III.
>Gen VI is OK so far, but it has some major copy/paste issue with ORAS. X/Y were nice, but it felt more like a tech demo for the new engine. ORAS added a lot of lore and interesting story elements, and the Delta episode was something I want to see in future Pokemon games. The actual game though has issues with too much of its content being same-y from X/Y and a lack of a endgame outside of Legendary hunting.