...For now it's just the "Grand Circle Tour of the Front Half of Main Street U.S.A."
OK, I now have a better picture of what you're planning. You might think about just putting a straight length of monorail track cutting across the very front of your layout. Your train isn't a bad model of the early freight train, so you might also think about getting a Schuco monorail. It will fit better scalewise, too.
I also have a better idea of what's going on with your track-jumping front truck. Unfortunately, you can't play with the track curvature, like when you're using non-roadbed track. So, you will need to tweak the engine itself.
One thing you can do is re-mount the pilot truck pivot to a swing link, the other end of which is pinned under the center of the pilot beam, or a little back from that point. This will allow the front truck wheels to avoid hitting the cylinder front on curves. If you do that, you will dispense with the pilot truck contact plate, and you'll need to cut away some plastic on the underside of the pilot deck, in between the cylinders. Also, cut back the sides of the truck frame. The wide truck frame tends to hit the insides of the cylinders on curves.