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Jeff shows tremendous courage simply by being able to make it through all the stuff that happens to him while he is with the Confederates. Here he is in a place where he could die at any moment if people realize that he is really a Union soldier and yet he can keep his head about him and survive. That clearly shows courage and confidence in himself.
As for initiative, how about him being willing to persist in courting Lucy when she really seems to be out of his league?
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