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In Paint, you can change the size of the image. If you look close, there are handles on the edges, they're just small, and not very obvious. Or, you can go to Image -> Attributes, and change the height and width there.
I like the back wheel idea more as well. The first image looks like it would be difficult to implement, but I guess you have ideas on how to do that. It seems like it would make very wide turns though.
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