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red and blue are difficult only for their buggy nature, which guarantee you at least some bullshit deaths. Leveling is boring to no end, but otherwise they are easy
yellow is the same as the previous, but with trainers having weaker teams and availability of the three starters makes it even easier once you pass the early game hell.
GSC are not difficult but extremely long. The sheer lenght is going to wear you down. Add also the lack of proper leveling pre elite 4 and you will get tired.
RBE are not hard, but the lack of the posibility to make a proper team hurts. You have your advancement blocked with no way of obtaining pokemon that can help you through common choke points such as gym leaders. The lack of physical and special split, coupled with lacking movepols hurt more than in the previous games
FrLg are the easiest of all
DP are difficult, but trainers having bad teams and coming less often make it hurt way less than platinum
platinum, oh boy, what a hell, already posted about it
HGSS the same about GSC is applied here, but a bit easier thanks to better movepols available
BW is not difficult, but the new mechanics of leveling force you to play intelligently. Forming a team with perfect coverage might take time but it is definitely possible. The elite four is quite chlenging and specially the second time
haven't played bw2, sorry
XY can be considered the easiest shit ever because of the weak trainers, lack of enemies with complete teams or powerful pokemon, early access to beasts with the mega evos and borderline easy leveling. That is, until you turn off the exp all, then you are up for a way more challenging game. Because the game was though with the exp all, not using it will leave you grossly underleveled and the double battles are frequent and insulting. It is amazing how much a game can improve just by turning off a broken feature
