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Milos is the guy who's always asking for cash at the gates so he can buy alcohol! 

Also thanks for the tip!!! I realized I wasn't going to the area where last man left the graffiti so I never even noticed it had appeared lol

Spoiler about Milos...

I think that once he as at 100% friendship, he will eventually die after a few days. He leaves behind an item, and then you get the achievement. I think?