Small Script Needed for Windows Tablet PC

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We need a script, executable in Windows, that will:

1) Randomly select an image from a set within a folder and present it in a maximized window with a plain button at the bottom that says "Go."
2) Upon the "Go" button being clicked, will replace the original image with another (always the same) image to be drawn on by the user and with a button at the bottom that says "Done."
3) Will, on the "Done" button being clicked, name the modified image with the current date and time and save it as a PDF to a target folder on our LAN.


a) We believe most images, such as jpg or .bmp, will work just fine; there should be no need to specifically code to a tablet pc.
b) Saving to PDF is desired but not necessary if doing so is a technical problem.
c) A web app is also okay if that is a better way to go.

Thanks very much for your interest. Please contact me with any questions.

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