Uploading a pdf is not a problem. You may have to check your file upload permissions under Host settings Advanced. Just add pdf or any other file extension that you want to be able to upload. I'm guessing some aren't in the list by default due to possible security issues like viruses.

I'm actually interested in getting a pdf to open in a new window as well. I currently have a link that will open the pdf file, but it opens in the same window which is "bad" because my users then have to hit the back button to see the site again. I guess you might want to consider this another UI bug, since some modules (like Links) allow you set the open in new window checkbox and others don't (like the links section of the add new page functionality).

It's "bad" from the perspective of the higher ups who don't want links to open in the same window. The problem with links to documents as I stated isn't really that their good/bad but just that the UI for DNN isn't consistant enough. Like I said you can specify whether to open a link in a new window or not when you use a links module, but no such option exists when creating a link from the "Add New Page" function.

Right clicking on the menu option created does not give the option to open in new window either. So I am still wondering if there is a way to create a menu option which links to a doc open in a new window. The only thing I can think of is to create a web page with the document inside it and then link to the new page I created, but there has got to be a better way. Any ideas?