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The Umar and Windspear quests can actually be quite difficult.
In my opinion the first quests you should do in Chapter 2 are:
Shadowthief quest
De'arnise quest
Korgan quest (After you did the Shadowthief quest, to save some time)
After doing these three you should have enough money to get to the next chapter or alternatively enough XP to do the rest of the quests (recommended, as that's where the fun is)
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