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I'm not sure this is really relevant, and I don't have any experience with Mathematica worth mentioning, but I just want to address part (1) of your question, about importing images to SAGE. If you use the Notebook interface to sage (in stead of a command shell) it's actually quite simple: open the [Data] dropdown menu above the worksheet and upload an image file to your worksheet. You can then insert the image in a text cell, as an html image.

Sorry if I'm only stating the obvious.