Mark, thanks for sharing the vision. Fun moving tracks after the fact, isn't it. Just a thought, would it make any sense to raise your town to the level of the trestle track? or maybe part way? Kind of hard to tell - with the piece of track ending where I think you had the Atlas bridge which you say will be connected to a rear track. (starting left of the window?)
Chicago has a bunch of places where a raised rail runs through city neighborhoods. Solid wall of material until you get to a major street where there was a viaduct. Talk about living on the other side of the tracks. This design effectively sealed off neighborhoods. To me trestles are for subways/ELs. In a couple of parts of the city, these former rights of way are now elevated strip parks.
