[haertig]

Do you need to keep a large number of eBooks on your Kindle? I use Calibre to organize - much more functionality there than any eBook reader - and then I only put maybe a dozen or so books onto the Kindle at one time. And over time, I change out the books on the Kindle as my mood dictates and I decide I really don't want to read that book I put on there last month as much as I thought I did at the time. As soon as I finish a book, I remove it from the Kindle so I can add another if I want.

I keep enough books on the Kindle so that I have several choices for my next book to read if I'm caught out somewhere and have to make that decision "in the field". But not so many that I can't see them all by scrolling the Kindle through two or three pages of listings (which requires no organization to work through). My Kindle shows eight entries per screen (I don't display covers). I am running older firmware, and newer firmwares may show more or fewer listings per screen.

The thing is, eBook readers are pretty terrible at organizing, the Kindle probably being the worst of the bunch. So don't try to make it do something that it inherently sucks at - don't use it for organizing. Some people keep hundreds if not thousands of books on their Kindles. I've never had any need for that myself. My friend does exactly that, everything he owns gets put on the Kindle - and he's always complaining that he can't find what he wants. Yeah, I believe that.

You already use Calibre. Given that, it's trivial to move books on and off your Kindle. Do your organizing and searching in Calibre. Then just put a small subset of your books on your Kindle. Enough to get you through your vacation or whatever, but not enough to cover the rest of your life.