>>55259308The change from Gold/Silver to Crystal is so minimal in my eyes that you get the same experience if you have Stadium 2, minus the static Suicune encounter and the Battle Tower + move tutor
Ruby/Sapphire have the eReader cards, international releases of FireRed/LeafGreen and Emerald have this functionality patched out because the eReader didn't do good outside of Japan. You can also make your own cards for both events (which im a faget did for mystery events) and even the battle e-cards. Progression of contests is also meant to be alongside your traveling in R/S instead of all in Lilycove like Emerald
Diamond/Pearl have My Pokemon Ranch, which for some reason did not update for Platinum despite it probably being something they could have done in an afternoon. Also, using Diamond and Pearl in PBR set the final boss properly
Black/White are mandatory to play first so you can use the Memory Link feature in B2/W2. You will literally miss out on a few battles and special Pokemon if you do not use this feature. Plus. Black Tower and White Forest are fundamentally different experiences.
Sun/Moon have the better/definitive story of the generation, Ultra Recon Squad muck things up and make it about something else by the very end
Of course if you do not care for these things, no one is stopping you from playing the third versions but I see these all as valid reasons why you would bother playing the first two versions of a generation instead.