I've now discovered 100+ locations and holy hell is the map huge! I also accidentally joined the thieves' guild, the dark brotherhood and the companions clan. I think I just randomly chose the right dialogue options, but whatever. Got some achievements for joining them.
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Also, a drug dealer was killed by a saber cat on the journey. He will be missed.
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Haha, was that the Khaijit trying to sell skooma near Falkroath?
