Welcome to PC. In my opinion, I find that the "third" installment or Yellow, Crystal, Emerald(Granted I prefer Steven over Wallace) and Platinum were better than their counterparts within their respective Generation. Yellow is unique because it diverges from the traditional Fire/Water/Grass start for an Electric one but otherwise is vastly improved(imo) over Red/Blue. Remakes or sequels filled in gaps or holes that the previous games had while introducing new mechanics(Abilities for FRLG, Abilities and Special split for HG/SS and Fairy Typing/Mega Evolution for ORAS). Black 2/White 2 are basically a sequel to Gen 5 like the Gen 2 games were to Gen 1 and basically change Gym Leaders and Champion in doing so(highly recommend giving Black2/White2 a try. Champion alone is worth it).
Curious if you've looked into the Anime at any point? Also got a favorite Pokémon or Typing?