Hmmmm..nag hulat ko sa uban mo critique pero murag wala pa man..so here is my take on this.
I believe your after for a photo-journalistic style of portraits. Well for me the first image quite sells the emotion I believe most people can relate to having traveling or being into a journey and I think its done what is suppose to do. The technicalities you mentioned is not actual that bad but it gave that photo its uniqueness.
The second photo does not say anything and for me this is a weak image.
The street style or photo-journalistic style photos implies emotion and has a story while the glamour/posed portraits implies beauty. I am very technical (lighting, shadows, background, etc.) on beauty and glamour shots but for photo-journalistic i look for emotion, composition and the story.
Just want to share a link an I think that might suits your kind of genre. What strikes me most is the topic about "Interesting vs Boring stories"
Objectivity vs Subjectivity: What Makes a Great Street Photograph?