Confessions, eh? Ok, mine involve ebooks.
I have a Nook. I buy ebooks from B&N, but also buy them from Kindle and other places. As soon as I've bought anything non-B&N, I download it, strip the DRM and convert it to ePub (format for the Nook). I then stick it in a folder with titles I've downloaded from B&N, before copying it to my Nook.
I'm not sharing the files. But I've also been around long enough to have seen instances where "big brother" has gone in and yanked files that were purchased legally. Damn right I'll back those files up.
If I get some other ereader in the future, I'll do the same thing with that.
I'm not really all that familiar with ereaders, but are they all that proprietary? If you have a Nook you can't ever read anything bought from Amazon without all that DRM stripping and hoop jumping (and vice versa I'd assume)?
Nooks use the open ePub format, so usually no DRM there. It's Amazon's Kindle that uses a proprietary format, and one of the very few e-readers that doesn't support ePub. It's one of the main reasons I got my wife a Nook instead of a Kindle.