Yes, something along those lines had occurred to me, but I am not interested in rooting something as basic as an e-ink ereader. It sounds like no company besides Amazon has set up something of this sort, for whatever reason. Being able to set up Calibre to email me the newspaper every day is a must-have for me. Now, if a competitor had a Dropbox-like service built-in, that might work, but it sounds like they don't.
