The beautiful thing about Pokemon is that you can start with any game from any generation. There's no big overlapping story or a lot of recurring characters, each game just adds to the history and fleshing out of the Pokemon world. Being a 90's child, I was into the Pokemon anime, cards, and home console games back in the day. As far as the main games go, I started with X/Y which does have some nostalgic elements for me so I'd say that's a good start.
If you're trying to learn the history, the controversies, the mysteries, the moves, type advantages, characters, etc. that have existed over all the games, Youtube will be your best source of information (definitely a better source than the anime). There are many channels dedicated to Pokemon. Just type in what you want to know specifically and guaranteed there'll be a page full of results.
I also go to this site www.pokebeach.com which is a good source of news and has a nice community.
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Topic: How do I learn about Pokemon?
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