Where should I start with Pokemon?

You can start with Sword or Shield, you won't miss too much, but a while ago the company that makes the games got a new Director and the newer games have different focuses on what they want to achieve as games, with the newer games starting from X/Y/AlphaSapphire/OmegaRuby onwards being more and more in the direction of being crafted for the story, while at least most of the games prior to them being much more focused on giving you an extreme plethora of repeatable and rewarding content that you can dump hundreds of hours into after you finish the main storyline, so if you're the kind of person who enjoys games that you can pour part of your soul into playing for ages and ages, you'll want to pick up the best of the best of the "old" Pokemon games, which means the ones you'll want to jump for are both Platinum and either one of Black 2 or White 2, and if you enjoyed Platinum enough to want more of it before playing B2/W2, check out either Heartgold or Soulsilver inbetween the two, whichever of those two you like the Pokemon on the box art the most is the one that I'd suggest for you.

Platinum was the masterstroke of the "old" games, it hit everything right at the time it was released and I would go as far to say it deserves the title of timeless classic, and Black 2/White 2 are unarguably the most fleshed out and finely-crafted of the games when it comes to quality content, and they've also got the absolute most content in total out of all the "old" games if you grade the content based on how meaningful, fulfilling and engaging it is rather than just purely volume of tasks and repeatable activities, because Soulsilver and Heartgold technically have more content in volume, but the way it's delivered to you in those two games ends up making it feel way less like anything meaningful and rather that it just ends up being part of the story.

/r/NintendoSwitch Thread