Meeting My Neighbors and Taking Their Portrait

I've lived in the same place for nine years...as far as I remember. I mean, I'm pretty sure it's been nine years. When I travel, I rent my home out, but I have been living here the majority of the nine years. Besides a few select neighbors, I have no idea who my neighbors are or what their life is like. I see interesting people walk by and sometimes I wonder about who they are. There are a few who walk by everyday like clockwork and I have a nickname for them, based on their style. I always look forward to "pirate" walking by and I hope to get his portrait one day. When I'm on the road, I don't mind approaching strangers since they will never see me again most likely but when I'm in my own neighborhood, I tend to avoid meeting anyone that is within viewing distance. It could be that I am pretty shy or might not have the energy to talk to anyone, or perhaps both. One of my photography instructors told me in front of the class that I spend too much ...