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Thanks for replying. I think I may have not been clear. I'll walk through the steps again using screenshots.

So here is an image of 780x640. The resizing of the canvas isn't necessary and I know how to script that so I'll skip that step on here.

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Next step is to create a layer underneath the image layer. (I can script all of this easily.)

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Now I can create an arbitrary line (I made it 10 px to make it easy to see what I'm doing. Really it will be 4px or smaller.) on the new layer. (This is where the "user input" is needed. And after done the user will use a short-key to trigger the next step.)

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The trigger will create a clipping mask on the top image layer. (Now this effectively create a strip, of whatever the user chose from before, from the original image. The different ways the line could be drawn is endless since the clipping mask will always only "choose" what the line goes over the original image. But lets keep using the line that I made for now.)

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Now this is where I need help. What is a good "one-size-fits-all" solution to take any strip at this point and figure out how to rotate it and cropped (Only the transparent pixels should be cropped) to where in the end you end up with this:

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I hope that helps in understanding what I'm trying to get. Again thanks for the reply.

-edit

I don't know why some of the images are showing up and some are links. So please click on the links to see what I'm talking about.