Modification Idea - Need some opinions

Kind of hard to get an idea without seeing it. Do you have some tacky clay or double sided tape to place the wheel where you think it will go and take a picture of James right side up?

I can't fit the wheels on without cutting them first, since there's a screw and that top half in the way, but I'll try and make a half-decent paint.net edit.
EDIT: Photoshopping in paint.net turned out to be pretty wonky, I'll just try and take a better picture later.