As you model this thing, remember what will – and, will not – actually be visible in the frame. I would suggest that you should very soon set what you intend to be your “final” camera location and settings, and block-out such elements as trees and buildings, all to scale. Make sure that the distance to distant objects is actually realistic unless you intend to use “forced perspective” (and, so that you don’t unintentionally wind up doing so). At this point the buildings might be cubes, but they should all be there, at proper distance and scale.
I see the front of one street-car and the front-and-left-side of the other. If that be the case, don’t bother to model anything that you will not see. Also, don’t bother to model details that you realistically won’t notice, unless at some point in the future you determine that you “objectionably actually do.”
The proportionate dimensions of the model need to be correct: my blush about your current model is that it is not long enough. Get actual reference photos of San Francisco street cars, determine their dimensions and be sure that your models match them. Or, if your exclusive goal is to match the painting, ignore this admonition completely if you decide that it does not matter to you. “What’s best” depends solely on the project and your objectives for it.