Here's a fun one -- I've got a georeferenced TIFF file with some linework drawn on top of it. When I print, either from paperspace or modelspace, to hardcopy, the image prints as a smooth area of light gray, with zero detail showing. The file _previews_ as expected, with the aerial looking like an aerial, but on paper it's just a smooth gray wash underneath the lines.

I used Rasterdesign to convert the TIF to a georeferenced PNG file, and had exactly the same result - good preview, lousy print.

Printing to PDF and then printing the PDF to paper works fine - I get a good looking preview, a good looking PDF, and a good looking hardcopy.