>>47352486The best playing order will always be:
>FRLG>Emerald>Platinum>HGSS>BW>BW2>XY if you're feeling adventurousThen you stop playing mainline games past that. You can then either go back to the Game Boy games to see what they were like or play the loads of good spinoffs this series has, such as the Stadium series, the GameCube games, Ranger, Mystery Dungeon, Conquest, Snap and New Snap, etc.
Maybe look into romhacks too. They aren't perfect but there's some fun ones out there that will at least satisfy the hunger for new content such as Prism and Gaia.
This is the best advice you'll ever get, so listen to it. Playing nu-Pokémon will just make you jaded like most people on /vp/, so keep yourself happy and don't.