I'll second CutePDF, and since I learned about it from Wendell, I have to point out that "Did I mention that it is FREE?"
IF you use Updox, you can print to Updox to collect and assemble the document pages in the order you fashion, and also make it a single PDF.
You could then send it through the portal as a PDF, so that you get a read receipt and they have to use their own resources to print.
