It's very cute and has a lot of nice little stories to tell to flesh out the personalities on the train in a realistic way.
I'm probably missing something, but I didn't much get the point of the die rolling whenever I was helping anyone and whether that really affected anything or not. I was able to complete tasks just fine even if I did roll a lot of 1's so I guess I might have gotten a "bad ending", but that's not readily apparent.
Nice entry and an interesting design.