So this is just an image, not a geotiff basemap or anything? How big is it? If it is exporting with default values, memory or something must be an issue. I would try restarting your computer so memory is fresh, then add each parameter you want to customize one at a time to see where it hits the wall.
You can also try setting smaller metafile/raster buffer size in advanced arcmap setting utility, to see if that helps.
Have you tried exporting the PDF with default settings?i.e.arcpy.mapping.ExportToPDF(mxd, str(output_path))
How is the TIFF image added to your map document? Is it added using the 'Add Data' button, or is it added using 'Insert > Picture'?Have you tried converting the TIFF to a different format (i.e. JPEG) and see if it that works?
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