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When counting all games in the series, I would say London 61 is the hardest due to the insane time limits, counting only 3D/HD games the hardest...

I can't say, I used cheats until IV. I did replay some of San Andreas without cheats and it's not bad difficulty wise though you can get...

Dragon Dance in Chinatown took me ages for some reason and was very annoying as it was a storyline pinch point. I am still really enjoying San...