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In my opinion it'd be Gen III. Although I don't dislike them, I just find them, boring... Its probably the worst part about Ruby, Sapphire and Emerald.
Generation 5 hands down for me. Each generation, other than 5 has one or two really awesome Pokemon, and then 1 that I don't hate, but don't like using. Generation 5 has nothing that I really like
In terms of design I'd say gen 3 - the only decent one is torchic. Swampert and Sceptile are just ugly, and I'm all for cutesy.
I loved the gen4 designs - torterra was awesome!!
Strategywise I'd have To say gen2's starters were the worst, with all evolutions being one type only (does grass/poison really count as two separate types?) :-
