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Welcome to PC! Honestly, the core gameplay hasn't really changed since Gen 1, they just added on things to make it more interesting like Abilities and the Fairy type such. There's a lot of new pokémon, sure, but it's still the same thing. X/Y is a good place to start, those games have lots of old pokémon along with new ones. Check out the Metal & Color Generation section if you wanna talk about Gen 1 and Gen 2.
I'm watching the old seasons of the anime as well, I only really watched Kanto and Orange Islands when I was younger but now I've seen Johto and I'm currently going through Hoenn. I don't know why I'm doing it to be honest, I don't even like Ash :v There's also a section for the Pokémon Anime if you'd like to check that out.
Anyways, I hope you have a good time here and that you enjoy the new generations, I always appreciate people trying to get into them with all the genwunners around.
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