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I've only got 449 books in Calibre so you'd think I'd put them all on my devices - but I don't. I only ever have 3 or 4 books actively on the go at any one time and I usually know from within a pool of say 50 or so what I want to read next. Actually I usually have the next 2 or 3 books "queued up" but sometime I go outside that.
I've got a number of devices I read from including PCs, my tablet, my phone, the android stick attached to my TV and of course my actual ereaders - so having the same to-read set on all is a bit of a hassle. I have a way of doing it with Calibre and Reading Lists but...
In the end I found I prefer to just select a few manually. Generally I have 75-125 on my ereader at any time. Actually since I have my Calibre library in Dropbox I generally don't even need to do that that often. Almost all my devices can download a file - apart from my Kindle. I can if I need to upload my books to my Amazon Personal Docs but I prefer not to with books I've deDRM-ed. So usually I either read Amazon-sourced books or plug the Kindle into one of my Dropbox-synced PCs. I suppose that's why I don't use the Kindle for travel as much as the Kobos.
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