We have not been penalized for "Printer Friendly Pages" at www.vortexventures.com . Google sppears to have tolerance for duplicate content in different media.
It has been our experience that "pdf" pages come in one PR lower than corresponding HTML pages with duplicate content, which seems appropriate enough.
What I would really like to know though, is how http://www.mezzoblue.com/zengarden/alldesigns/
and other sites get away with multiple exact HTML pages in different designs while maintaining PR7-8s all the way thru? --- and what about 300 or so links on a single page when GOOGLE recommends no more than 100?
Are there special exceptions after joining the top 100,000 websites? Do the alogrithms change as popularity grows?
Are there different sets of rules at different popularity (traffic) levels?
We believe there are.