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I was the first one in my class to get a Pokémon game when I was 8 years old. First game was Red. I guess I've been playing this game for over 15 years.
Gen I was okay, maybe more mediocre in retrospect. I've always hated Grimer, Muk, Voltorb, Electrode, Magnemite, Magneton, Dugtrio, Jynx, Hypno, Machoke, etc. These ones irk my mind just thinking GF did nothing to make them better (I mean, apart from Magnezone which completely corrected that line, thank God). I've always loved the more animal-like mons, though.
Gen II was the best gen because there were zero of these hideous "man-made/man-shape" mons. Johto just felt cosy and all around nice. Plus I got to fight myself from Yellow, so that was pretty cool too, probably the most pleasantly surprised I got in a Pokémon game.
Gen III is a good gen but really lacking in fire types. This trend would continue on to the next gen. I suspect most exaggerated love and pandering for this gen (I mean it's a good gen, but it's no gen II or gen IV) comes from people whose first Pokémon game was either Ruby or Sapphire. Because other wise it's a pretty midterm gen for me. I guess they did introduce the first desert, but otherwise, 2muchwater4me.
Gen IV is a really great gen. First it's an amazing region to explore, filled with caves and snow and all around good hiking/exploring places. Second, for giving all of those mons much needed evolutions. I don't understand why people hate them so much, they're literally perfect for those mons (say what you want about Lickilicky, but it's a perfect evolution for Lickitung). The only thing I dislike about this gen are the legendaries (just too much, seriously).
Gen V is a complete reboot for the series. In that sense, it's a Gen I.2. It ends up reviving the stereotypical mons again, it's a shame most of them are really shitty. The story is great, though. B2/W2 are probably the best Pokémon games we have right now.
Gen VI is boring. I guess it looks nice, but that's about it.