Hoarder, it's not for me to say what another photographer should or shouldn't do, or what should hold their interest. In my own head, this changes frequently. Whatever feels right for you is right. I hope the following three photos illustrate one approach that you might like. Often, if I see someone interesting on the street I simply ask if I can take a few photos. Worse can happen is someone says no. Sometimes "no" can be funny, for example in the case of a woman with wild hair who said, "I hate photos." Which is funny because it begs the question, did she have a bad experience with a photo? Anyway, these photos are of Jerry -- a 24-year old self-proclaimed actor and musician. I ran into him on 42nd Street near 9th Avenue in Manhattan, NYC. He and a friend were on the way to catch a bus to upstate NY. When I was 19 I too traveled cross-country with a backpack and a pair of dangling boots. I asked Jerry if we could shoot a few photos. As you can see, he was into it. My point is that you can start off asking, and then if you feel comfortable, shoot candids. I think people are too busy with their own lives to care much if at all if a photographer shoots a few photos of what anyone can see with their eyes.
Hi Dan and thank you for this great advice. Your photos of Jerry are brilliant, I'll certainly start asking and hope for the best. Love how this was a reminder for you of your journeys aged 19.
(It was also a reminder for me of a fab 10 day trip to NYC in 2006 staying at the Harvard Club on W44th).