Doomsayer

Background
You first encounter this man in Lothering.

This fellow is standing near the Village Chantry, talking about repenting. The Warden can talk to him and there are several ways to send the guy away for a while. He will stay away until you leave and re-entered the area.

Strategy
Lothering encounter:

It is possible to earn some money without penalties. You also talk to a chanter during the same cutscene, after talking with the Doomsayer. The chanter comments on what the Doomsayer says and asks, "He was right, wasn't he? There's no hope for us..." If you select "That's right. No hope for any of you fools!" you will then have another set of speech options where you can select "Give me your valuables, and your sorry lives may be spared." The cutscene ends and the rest of the people leave for the north. You receive 45 silver. No penalty. Redcliffe encounter:

You can intimidate, persuade, and use more ways to send him away for a while or just kill him and have him gone for good

Result
If asked for from the chanter, 45 (Lothering)