A big problem with Paperport running under Crossover is that a Mac's scanners aren't visible, nor can they be installed in a Windows-like fashion. However, it's possible to scan into Paperport indirectly by using Image Capture, which is standard OS X software.
Among other things, a user of Paperport can browse to view file hierarchies, folders, and contained files, so in Paperport, select a folder into which you want to scan a document, then use Image Capture's Scan To | Other... to choose the same folder. When you scan a document using Image Capture, it will be available to Paperport. (You might need to change folders then change back for the display to update.)
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