I've uploaded a pdf file and copied the path. I then created a helpful guides window and linked the guide title. When I click on the guide, it goes to another page labled "<name>guide" and that's it. How do I get it so my guildies can click on the guide and download the PDF?
You have almost everything setup properly. The thing you missed on the "Static Menu Item" edit page is the checkbox for "Is this just a link to another page."
Go in and check that box, and then your links will point directly to your PDF files.