As mentioned previously, setting the difficulty to Easy works best to make the game pacing flow as fast as possible. If you've ever played a third-person, open-world game, Watch_Dogs shouldn't be much of a change of pace.
There isn't a specific path you should take in terms of working on the different kinds of missions and side content in the game, so feel free to start wherever and end wherever. The same goes for the skill tree, for the most part.
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