I updated the topic subtitle to ...Brick Street Extension... to focus on the current discussion. Last evening, I had another idea that I finished mocking up today. It is actually similar to what I envisioned when I first started placing buildings on the town area months ago. A twisty turn at the end of a street as it leaves town is quite common in my experience. I mocked up how the road could cross the two higher tracks and still allow trains to pass underneath if I keep the road back far enough and make it very thin. 
No, there isn't much clearance. The stack on the Decapod makes it my highest engine and that one boxcar is more modern than I like, so I don't anticipate getting anything higher. I could push the the road crossing back a little farther towards the corner.
I put the road going into the tunnel/underpass again. The steep bank from the town to the road below is reminiscent of the way we have to travel from our house into town. Of course if I want to use that scene, but have a gentler slope, I could move the road to the left any number of places. While the next spot to the left is a little too narrow, it is reminiscent of the places that go under the former B&LE I mentioned a couple days ago. 
