If you're using collections to track books by series, do investigate Calibre's plugboard options. With them you can prepend the series information including position to the front of your books as you transfer them to your Kindle (or other reader). That works well for me with my Kindle Voyage.
On the other hand, I own a Kobo Aura HD as well--and really like it. I don't have problems with it crashing and I like the customizability. I appreciate the ability to easily use collections with Calibre, the ability to use my own fonts, and the much more granular user control over font sizes, margins, and line spacing.
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