Why am I not encountering the informant after executing Simon's event on the 2nd layer? how to continue this quest?
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Go to the 2nd layer, he is at the campfire, there is 2 campfire, choose the one without Randel.
After that, there will be guy in the pub telling you where Simon is.
AND after that, this is the last, go to the Mine by riding on the black carriage in front of the Dungeon gate, Go all the way to the upper right, turn left when you see a dead end.
Before the last, if you want a good ending for Simon, talk to the old man in the second floor of the Church, keep giving him what he asked. (Hint for the oldman quest: do it at night or just in the dungeon)