I would love to find a plugin to manage document uploads and link insertion... so...
Maybe a control panel to upload .pdfs (or .docs etc), and assign them a friendly name. Also an option to set the css formatting for the document links when inserted.
And then, a dropdown at the end of the quicktags, to select your documents by their friendly name, and insert a link into the post, using the css formatting that was set in the control panel.
Anyone up for the challenge?