For me, as long as eInk readers are black & white (great for reading!) and relatively slow (i.e. marginally slower than a computer - not a problem when reading, but makes browsing large collections time-consuming), I don't think I'd even want more than ~200-300 books on a reader at any one time even if the reader can handle it without crashing, just because browsing on a 6'' black-and-white screen on a relatively slow device is not my idea of fun.
When I don't know exactly what I want to read next, I'm not going to need search (for author/title) - I want to browse. Titles will do (and is what I do on the Kindle) but when I'm really unsure, I admit I prefer to browse in (full-colour) cover view on Calibre because that can sometimes give me a better "instant" idea of what the book's about, at least genre-wise, and of the tone. Also, having blurbs/descriptions right there at hand instantly is a plus.
Basically, as long as ereaders don't let me do that, I have no real desire to have my entire collection (which is not as large as some people's, but still over 1600 books) on my ereader. I do appreciate that other people pick their next reads in a different way though and the idea of having your entire library always with you can be very appealing - for me, it's just not practical (and again, 99.9% of my reading is done less than two feet away from my computer which is one of the places that houses that entire collection so it's always at my fingertips anyway).
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