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3=4>5>2>1=6>7>8
Between the fairly cohesive yet diverse regions with plenty to explore, important changes to battle mechanics, overall decent new pokemon in good quantity, contests/battle frontier added more ways to play with your pokemon, wide variety of good spin-offs, and fair amount of challenge 3 and 4 were peak pokemon. 3 had better regional dex balance but getting cut off from gens 1+2 and splitting the natdex between games so you actually needed to have bought every game that generation or traded with someone for the exclusives from the games you didn't have was a low point, no online yet made mythicals and general trading a pain but thanks to the 10th anniversary there were a lot more distribution events than previously and the extra effort required made it the most rewarding natdex completion experience, and it was the start of the story interrupting gameplay instead of being part of it. Gen 4 got online which made it much easier to play together and distribution events were much more widely available but battles ran pretty slow, power creep started becoming a real problem, and since some later ds models dropped the gba slot you had to either run worse/multiple systems or miss out on palpark which was more fun than bank but also a pain in the ass with the transfer limits. Gen 5 fixed a lot of 4's issues but got a bit more hand-holdy with all the healing npcs and the story took precedence over game play in a lot of spots although it was a better story, still slow, no in-game events for catching mythicals after victiny although they got some story stuff, musicals are downgraded contests, battle facilities lost some variety, and it's the most linear region. The rest were either building the foundations or were active down-grades to the overall experience.