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To unlock the guy's capers, you only need to follow their main adventure, you don't actually have to do any of their capers. So, to unlock Roland's India caper, you need to do the 'Drop in on Roland' etc events, but you DO NOT have to do Roland's Egyptian Adventure or Australian Adventure. This is a common misconception and it makes it significantly easier once you realize this and can skip guy's capers.
While it isn't recommended, it is possible to get the Maximally Wily and Social Butterfly achievements in the same play through. It requires very specific choices and precision, so it isn't recommended unless you are a very experienced player.
All attributes have more than 100 points, so there is a bit of leeway. For example, you can get at least 103 Wits points.
Capers that require another to be completed before hand:
-The second Serpent Empire Adventure requires the first Serpent Empire Adventure to be beaten before Peru
-The Albino Alligator Adventure requires you to beat The Main Adventure in Peru
-The Great Game Adventure requires you to have seen all of Roland's Main Adventure scenes up to India
-Guy's capers unlock if you are following their Main Adventure line, not if you do their 'Adventure with blank in blank', so you just have to do the 'Drop in on blank', 'Meet up with blank', 'Watch blank cause mayhem', etc, events.
-Do note, a lot of capers must be activated in New York before you can do them in another location, but they don't really have prerequisites per say