I might fit #1. Though I grew up in what many would call a ghetto, I never felt I lacked anything at the time, and the basics (food and shelter) were always covered by my parents who, while acknowledging that things might be tough, were always optimistic for our future.
#2 I'm not sure. I never felt myself as a "misfit". However, I did have the confidence of my convictions so sometimes would take a stand on things without being obnoxious about it, and was willing to adjust when I was proven wrong. DW said that was what attracted her to me during college - she saw me as someone who was popular but not a crowd follower, who got along with folks whom I disagreed with. Perhaps that helped in life to focus on the goals I wanted to accomplish without worrying if I was doing better" or "poorer" than my peers.