Matt,
First off, good on you for experimenting! In terms of comments on the image and presentation, I'm not sure technical analysis is what you want, but my biggest comment is to watch your lighting! Most of these photos have nasty down lighting from the train's lights, which gives unflattering shadows, which can be used to effect depending on your intent, but I don't think it works here. Obviously to overcome this you need more fill flash (softboxes are a bit inconvenient for trains

).
image #1 (LHS)
works. It's powerful and engaging, and the offset subject gives a contrast between subject and OOF background. Reflections in the sunnies add to the image. Nice, but needs more flash to offset the lighting as discussed above.
image #1 (RHS) doesn't work as well. It's still ok, but in the background my eyes are drawn towards the back by the cascading seats, whereas in the foreground my eyes want to follow Sam's and go to the side. Reflections in the glasses are excellent. Needs more flash.
image #2 (top) doesn't work for a few reasons. Blown out forehead, nose and cheeks. Distracting object on the left (I think it's a girl with dark hair, but it could be a psycho in a balaclava, aint DOF great

) would be better left in focus for this reason. Light directly above her head... hmm, not sure, this could work, but will distract from the subject more of the time than not I'd think. Pose is fine and the geometry of the scene works.
image #2 (bottom) Not bad! The lines in the background (seats and lights) work great here. Balaclavad psycho in the background again. Blown out nose and hair though (or did she get highlights

, gg cheap puns).
Anyway I hope I didn't give you more technical than you wanted or needed Matt!