If you have the file manager enabaled, the link tool will have the option to browse the server and an option to upload new PDFs
I'm not sure what I am supposed to be seeing in the screen shot?
Your friends over here at WebAssist! These Dreamweaver extensions will assist you in building unlimited, custom websites.
These out-of-the-box solutions provide you proven, tested applications that can be up and running now. Build a store, a gallery, or a web-based email solution.