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I also use Calibre for a few books and agree it's a very usefull piece of software, but, most frequently I just use the send to kindle email.
- I drop my O'Reilley books into Calibre and a few misc. sources (material I which to keep).
- For Fictionwise books I just use the send to kindle e-mail feature from the site itself.
- Books and my HBR subscription from amazon go the usual wifi route.
- Articles on the web also take the kindle email route via a Chrome extension.
- Work-documents and misc. also take the email route to the kindle.
- And also the amazon send to kindle windows software for items downloaded via the browser (typically read-once and discard material).
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