[Semaphor]

You can manage your collection with Calibre (and at least used to auto-strip DRM in the process) without jailbreaking, I did that with the Kindle Keyboard many years ago.

The only thing I remember about jailbreaking, was being able to use custom screensavers and fonts.

[QuikAccount]

I don't think you can strip DRM any more. At least I can't with my Kindle Paperwhite and Calibre.

[joecool1029]

You can still, but unless the libraries needed to do it are updated you'd need to use the last version of Calibre built on python2.

[coconut08]

I didn't have any issues removing drm from my purchased amazon books as of a few months ago using the latest version of calibre released at the time and the latest version of the kindle for windows app.