Multiple issues with ADE

I borrowed a book from overdrive, then tried to sync it over to my ereader.  Upon clicking I keep on getting this error.

1.  "Your eReader is not authorized to open this book [and] is protected by Adobe Digital Rights Management (DRM). Because you previously deauthorized your eReader, you need to re-import the book using Adobe Digital Editions (ADE)".

2.  I tried to deauthorize, authorize, re-import and re-copy the file to my ereader through ADE, the same problem.

3.  After trying more then 10 times, now i'm getting 3 copies of the book on my library even after i try to uninstall and install ADE.  I don't see this files on my mobile version of ADE.

What is the easiest way to resolve these authorization issues?  It's very frustrating as this application of your's is not so easy to use and when you hit these types of issues, you end up unable to proceed.

Can the Adobe engineers fine tune the authorization process?  It seems that there are some files which are left somewhere (cloud / local machine / eReader) which is causing these problems.