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1st gen: Fun when it started, now it's become increasingly harder to play.
2nd gen: Let's spend hours meticulously trying to beat one damn person with the shittiest level scaling in history and make the first region a barren shithole. Other than that, fairly good, kicked off some decent mechanics.
3rd: Pretty awesome, good designs and world, wishing it had slightly less water and more things to do on land. Has the most adventurous feel to me.
4th: Slow, bland, Platinum is king of this generation, no question. At least it bothered to fix the flaws of the first two games. HG/SS can fuck right off after doing nothing to improve the game(s) it came from. Except following Pokemon, I guess. That was cool.
5th: Too linear, B/W2 was just what it needed despite being an overall expansion. Designs are...Idunno, good? Based Infinite TMs were introduced.
6th: If there's no infinite TMs, I walk.