I suppose there are a few debates regarding OS on an e-reader:
1) Looks
2) Efficiency - page turns, smoothness, speed, resolution etc
3) Features - menus, Toc, sizes, etc
4) Formats it supports (epub, mobi, pdf etc)
5) Import / Export - how to buy, load, get. etc books.
Personally my main thing is features! I do everything I need to the book in Calibre and get the book into the e-reader however is necessary. My issue is with the lack of readability with expandable TOC's in most OS's.
I would say that if you have a computer, then that is a great help in organising your e-reader. If you want to be 'self sufficient' with an e-reader then wireless and digital book store accounts etc are going to be much more important.
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