I chose mine for what it could do. At the time it was the only reasonably priced device that allowed annotation, highlighting, cross-document search, and wireless downloads.
However I wouldn't have spent the money if there hadn't been a well-stocked online bookstore with cheaper-than-paper prices, or if it hadn't been offered by a reputable company with a history of good customer service.
About the only thing I didn't consider was e-book format. At the time, ePub was a gleam in some committee's eye. Nowadays ePub support might cut some ice with me, but only if the DRM for all the major e-book stores that sold ePub was reliably interoperable on all ePub devices, and only if the selection / prices were at least as good as what I've got access to now.
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