>>58044881 (OP)I'd recommend going like this:
Heartgold/Soulsilver or Crystal (depending on if you want something closer to what you experienced with Pokémon Yellow, or a “newer” version with some improvements and more stuff to do) Emerald or Omega Ruby/Alpha Sapphire (imo Emerald is still superior, but you may prefer something more recent) Platinum (definitively the best Sinnoh experience) Black/White Black 2/White 2 X/Y Sun/Moon or Ultra Sun/Ultra Moon (story-wise, the original SM are actually better, but USUM add a ton more Pokémon to the roster and a bit more side content. But don't play one and then the other, as that'll just be a slog) Sword/Shield Legends: Arceus (adds just a few more Pokémon, it's not a new generation, but honestly it was really fun and a nice experience. Though the Legends games aren't technically? part of the main series, so you may want to skip it if you want to) Scarlet/Violet.
Essentially, what
>>58045013 said, but with a few more addenda. I'd heavily recommend going to each game's Bulbapedia article to judge for yourself what you'd prefer to play. Also, don't rush through them, but take your time trying to appreciate what each of them offers.