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My choice for first playthroughs:
-Blue
-Silver
-Ruby
-Leaf Green
-Diamond
-Soulsilver
-White
-White 2
-X
-Omega Ruby
-Moon
I know Ruby is an outlier, but there's a dumb reason for that. I was going to pick Sapphire, but I was like 10 and my friend picked Ruby, so at the last minute I changed my mind to match. Then a decade later I autistically picked Omega Ruby for continuation's sake.