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You need to skip the Emerald in the Northwest if you want to do everything in one playthrough The catch is, you cannot finish them all for a trophy. The goal of this chapter is to raise 20,000 gold which is exactly what you will get when you finish all 3 quests from the Thieves Guild. This chapter should only take about 1-2 hours to finish You need to do this right away, and if you talk to the Queen first, you will lose Chest. Once you leave the first dungeon, make sure to immediately go earn the Man of Shadows trophy. This is a great spot to initially level up A hole in the wall at the end leads to a fire which heals you fully and you can save. If you can make it to the end of the first dungeon, there is a great spot to level up. In the beginning, make sure to buy some herbs because Anders is very weak. You can earn the following trophies in this chapter This chapter should take you 3-4 hours to finish Make sure to read every book case you come across in the 5 towns for another trophy as well You can also recruit monsters as well so this trophy is not as hard as it seems. You can equip weapons/armor you find, also you can buy items from the shop to assist you. There is a trophy for not buying anything from these shops. While playing through this chapter, DO NOT BUY ANYTHING FROM WEAPON OR ARMOR SHOPS. If you get stuck anywhere in the first four chapters, check out this guide. Chapter 2 - Man of Shadows With a little help.Minimum number of playthroughs needed: N/A.