ADE won't copy to Nook

Start by saying I've used ADE before to great success.

However, my newest borrowed book will not copy to my Nook.  Copying will either not start or I get "copy not responding" message.

Yes, everything is authorized.  I've downloaded the newest version of ADE (4.5.10) and still the same problem.

To top it off, I've tried downloading the ebook from the library again (thinking maybe that is where the issue was) and now 7 copies are showing up in ADE.  I can't get rid of them.  I deleted from the computer and "remove from library," but all 7 keep showing up every time I open ADE

Please help