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I also manage my books using Calibre as it coverts between formats and the only format that plays nicely on a Kindle is MOBI. Any PDF or EPUB or text or doc format books I have I convert to MOBI with Calibre and it is very easy to manage my library on all 3 of my Kindles. Except for the books with DRM.
I found a plug in for Calibre that strips out the DRM for MOBI format as a book is imported into Calibre. It does not work on books already in the Calibre library, they have to be deleted and re-imported. The plug-in I used and how to use it is at http://apprenticealf.wordpress.com/2012/09/10/drm-removal-tools-for-ebooks/. I got this to work on MOBI format without much difficulty. The biggest problem was finding the correct download button among the spurious software on offer.
I also buy books from other than Amazon and a lot of these are in EPUB format, also with DRM. They are perfectly readable using Adobe Digital Editions on a laptop or desktop but I want them on my Kindle. The EPUB DRM stripping did not work using the above plug-in as there needs to be a file called adeptkey.der in the Calibre config directory. This file apparently hold all the keys for EPUB DRM.
There are detailed instructions to generate this key file in Linux using python and python scripts. It entails installing python under Wine and then running the scripts under Wine which use Adobe Digital Editions to generate the key file. Some instructions are very specific as to which versions of Wine, Python and Adobe Digital Editions to use. I could not get the process to work without errors. I struggled for 2 days with this, getting threats of divorce and physical violence from SWMBO, until I understood what I was trying to do. The key file is not system specific, it can be generated using windows and then used in all Calibre, so I ran the procedure under windows XP in Virtual Box and generated the key file first try, no problem. Pasted it into my Linux Calibre config and the DRM bit the dust. I used the Python and scripts download from http://www.epubee.com/remove-drm-from-epub-on-adobe.html .
I now have all DRM free books in Calibre which I can load into my Kindles or tablet or anything else I care to use, (until I find a format that doesn't work). But what a hassle to use what you've paid good money for as you please.
George -- The Mailing List for the Devon & Cornwall LUG http://mailman.dclug.org.uk/listinfo/list FAQ: http://www.dcglug.org.uk/listfaq