Hi Isaiah,
I wanted to share that I really enjoyed the film overall. The pan up from the locomotive pilot was especially nice and some of your camera angles were very effective. I loved your music and film independently, however the two together left me with a somewhat disjointed overall impression.
A quick note on the music (pun intended). Swing music like you have used (Count Basie's Jumpin' at the Woodside as performed by the Benny Goodman Orchestra for those who are curious) is often used in films dealing with railroads and transportation. Many use it because of its perceived value in evoking a sense of nostalgia. However, big band swing like you have selected is more often associated with urban settings rather than the more bucolic setting of the WW&F. In addition, in terms of era many would say the swing era began around 1933 and its prominence in musical culture was solidified by 1935 Unfortunately, since the WW&F stopped operating in 1933, it is unlikely that anyone ever jitterbugged on the platforms while waiting for a train. So the era of the music and the era of the railroad is again a bit disconnected. Try pairing it with some music of a more rural origin such as fiddle music, folk tunes, etc. and see what you think. Hopefully you find this helpful!
-Steve Piwowarski