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https://docs.google.com/spreadsheets/d/1kk1nVwdcqxsqkysRpLgMoRE0wKDOmMXYfxKpDsBlmas/edit?pli=1#gid=880947664
You can find a lot of answers here. Reaching 100 like don't do anything for now. About catching opponents - you must use more than one lure.

I am looking at this and I cannot find a way to trigger the Scar event. Its already Day 33 for me and I have had no luck, even after talking about the corrupt guard with the tavern keeper.

As you see in the guide, you have to be on the road during the night. I don't remember which option you have to choose, but at a moment, the scene wil trigger. You just have to be a bit patient ^^