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>Gen 1
Didn't think too much on it back when I played. Messing around with glitches now is fun and I can enjoy the simplicity of the flow and an iconic Pokedex.
>Gen 2
Still my favorite. The idea of going back to Kanto after beating the Champ blew me away as a kid. The color scheme, day/night cycles, and music were top notch.
>Gen 3
Also great entries. Going to the GBA graphics was a notable upgrade in the visuals department and I like a lot of the Hoenn pokemon. Having two villain teams was a cool concept and even though I sucked at it, the Battle Frontier in Emerald offered lots of replayability. Hoenn was fun to explore and I never minded the water routes near the end.
>Gen 4
Basically the dividing line of 50/50. Didn't care much for DPPt with how slow everything felt and the excessive HM requirements. The Phys/Special split was nice though. Thankfully, HG/SS saved this Gen for me.
>Gen 5
The sleeper hit Generation for me. Played Black back when it came out but didn't think much on it while skipping B2W2. Once I played the sequels years later I fell in complete love. I could appreciate BW's use of only new pokemon once I had more time to enjoy it, loved the protagonist designs and the themes of this Gen. B2W2 has one of the best variety when it comes to regional Pokedexes and the Habitat list was an addictive feature.
>Gen 6
Another sort of "meh" generation of enjoying the remakes more than the new games. Still haven't finished X despite picking it up on release and starting over multiple times to find the spark of Kalos. ORAS were fun if a bit handholdy and I liked the DexNav a lot. Lack of a Frontier is a shame though.
>Gen 7
It was fun to go through once but I have almost no desire to pick up Moon to playthrough again due to the cutscenes and handholding. It has its moments, but none I'd need to relive so soon. Best case scenario is USUM gives me another B2W2 rush but I'm not holding my breath. No preorders on them right now.