I attached the cowboy to his base. Not bad!
I also made some adjustments to the railing. I 'broke' one of the spindles and leaned it to the side. I also shortened the side pieces and put caps on them. Here's the result.
And here's what he would look like, more or less, with the railing in place.
It's a little taller than it would be, as I'd trim the corners off the floor boards and set the posts down under the floor. I haven't decided if I'm going to use it or not. It's just be in the way of painting him right now anyway, so I'm going to leave it off, do the painting, and decide later.