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Criticism is not my forte but I will give you what I can. You have obviously committed yourself to this project. As far as the composition, the scene which you have created (outdoors, wide open, gone with the wind) seems better than the reality of the photo. But even with the vertical aspects of the (in town) bar added (which I think would be needed to explain) the lady and the bar seem a little incongruous. Possibly a picket fence would be more in keeping with the mood you have created. It's a little late for this suggestion but straightening up her posture, and showing her as just standing indoors (arms out as shown) with a simple background, that might have looked nice.
Show your painting to someone without the photo and see if they can explain the scene to you.
I look forward to other folks suggestions. I can appreciate that the pressure can be great...good luck with this.
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Mike McCarty
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