Why should the grandparent jump through the hoops though?

Also, isn't stripping DRM from Amazon ebooks against the TOS? Potentially exposing him/her to some legal trouble?

O'Reilly will put your ebooks into your Dropbox folder if you let them. Amazon could do that. Problem solved.

Link: http://shop.oreilly.com/category/customer-service/dropbox.do

Backups are 'jumping through hoops' now?

As others have said, breaking the DRM for personal uses (backups, changing devices) should be perfectly legal in the US and probably most of Europe as well.