Create a temporary playlist. In the Library view, select all the songs you want to check or uncheck. Drag them to your temporary playlist. In the playlist, command-click on one of the checkboxes. The changes will be reflected in other views, including the Library. It's not the ideal way to do it, but until Apple adds "Check/Uncheck Selected Songs" menu items, it works ok. BTW, you are asking about the OS X version in the iTunes Windoze forum.
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