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I voted for Alonso's challenge. I kind of suck at Monza, the AI seem to take the corners much faster there and I have to manage the understeer of the car. So you have to be 1st by the end of the first sector and play the blocking game from there on. Not only that but you also have to make sure Alonso gets 2nd place.
I found Button's quite easy actually. You really have to take the title literally, "Gently Does It". All you have to do is be gentle, doesn't matter if you can't keep up, just try to reduce the time lost by keeping it on the road. By the end of the second lap you'll start to pick up speed and on the last lap no one should be able to stand in your way... I went from 10th to leading by 10+ sec on the final lap.