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>Gen 1
Fire Red and Leaf Green not letting you evolve golbat, onix, etc. was really fucking stupid and there is no good reason for it, limiting the player for no reason or because muh original 151 sucks, none of the evolutions are so good they'd completely destroy the game. and for gen 1 specifically, the abysmal movepools of a ton of the mons in the game.
>Gen 2
Trainers in Kanto having pokemon that are level 30-28 when you should be well above that by now, it's really dumb and means you automatically steamroll all of them when you get there. This plus the levels of wild pokemon being the same as in RBY make it a grind to get to Red's level.
>Gen 3
Lack of pokemon variety in water routes despite them making up half the region, so many interesting encounters are locked to be fishing only so by the time you're surfing for half the region all you'll find is Pelipper, Tentacruel, and MAYBE Wailmer and Sharpedo
>Gen 4
Retarded decision to limit the original dex of Diamond and Pearl to 151 pokemon because KANTOOOOO, tons of new pokemon can't even be obtained till postgame in Diamond and Pearl because of this
>Gen 5
Pokemon's evolution levels being tied to the level curve in Black and White. So many gen 5 pokemon evolve at ridiculously late levels, and the majority of them don't even have pseudo legendary stats or anything to justify it, it kills a lot of their viability in later gens too
>Gen 6
Lumiose City, the camera in this place is nauseating and makes it ten times more confusing to get around in than it has to be. Also the Elite four only having four pokemon is fucking stupid and they, the Champion, and every gym leader in Kalos are a joke.
>Gen 7
The bombardment of cutscenes, there are way too fucking many and they make trying to replay Sun and Moon an absolute chore
>Gen 8
The story of Sword and Shield actually feels like an after thought, everything with Chairman Rose at the end is embarrassingly awful and abrupt