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Gen 1, needless to say, was the start. Brand new franchise learning to walk. It was great, but had some minor problems, as is to be expected.
Gentoo was an incredible sequel. a bunch of new pokemon, some from already existing families. and new types and loads of other essential additions. Learning how to make pokemon feel like pokemon.
Gen 3 was the graphical leap. comparing to today even these games look alright. a little rough, but compared to GBC, the GBA was almost perfect. More pokemon and they started experimenting a bit. nothing too outlandish.
Gen 4 was the last true pokemon generation. phys/spec split, and polish the visuals. very memorable region with great music, great areas and lore, and even more and more pokemon. started racking up a little too many legendaries, and the games were sluggish at times. These shortcomings were often improved as more Gen 4 games were released.
Gen 5 while many may believe started the decline, wasn't too bad itself. To me, I believe these were the peak, but I'm gonna try and not upset too many people with this. Region layout was very basic (go in circle), but the areas were really charming and the music oh my lordy the music. Introduced that cool red HP music which was never brought back. Added that charming little animation for the pokemon to make the game feel more spirited and alive. the games were smooth and the pokemon had some cool concepts
Gen 6 was the largest plummet. I personally feel they rushed into the 3D because of the 3DS. Player models were ugly, and the models overall were bland. The games felt a little childish. Specifically XY. Music felt uninspiring. Not fond of the 'mons either.
Gen 7... idk. It's too different for me to say anything on it. Still feels childish. maybe i'm just growing old.