There was a lot in this and I think one of my new favorite lines, “He had a balance to his features that implored a strangers’ trust.” (although there’s a typo, a stranger’s trust). That is about as good as a description I’ve ever read and I immediately knew what you meant.
Five pencils, and I’ve put a follow on you. You gots moxy!
The beginning had some run-on or just overly long sentences. I liked the hints in the middle there about what you meant in the beginning as well. The last bit really summed up the point of the challenge, I thought.
This is a nice take on the challenge. It shows how we can assign details and stories to people that are completely unknown to us. We write fiction for strangers by making judgments and assumptions about them. Well written.