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Original post doesn't say which Kindle is being used. If it is K3 or later (i.e. with Wi-Fi capability), I just email the calibre newspapers automatically everyday to my free kindle email, e.g. "username@free.kindle.com", which is only delivered via wi-fi, not 3G. There is no charge from Amazon for wi-fi delivery. Of course the old transfer by USB works fine if you're at home. Of course, if your Kindle doesn't use wi-fi or you have no wi-fi router at home for daily use, you're out of luck on that.
The other advantage of the email solution is that now anything you email to your Kindle address (free or otherwise) is stored on your Amazon Kindle cloud and will show up almost immediately in the Archive folder on the Kindle, where you can just click to download them. That's great for books you email, but a blessing and a curse for newspapers and magazines from calibre. They're ALL there. You'll find every copy of the New York Times you ever emailed from calibre, and, unlike the Amazon subscription version in the Archive folder, there are no dates showing. I think today's issue would be the last (or first) in the list, but finding a specific back isuue would be a bit of a challenge.
A similar email situation is to auto-email the calibre news to some other address you can access on the Kindle. They show up as an attachment which can be easily downloaded. In addition to sending news to my Kindle free address each day, I also auto-mail them all to my blackberry address where they are opened with mobipocket reader. (It's an older phone, won't take the Kindle app.)
Another alternative, though I have never used it, is that calibre itself functions as a server. You need to log onto its server address from any browser and your entire library is there for the taking. I presume you could do that from the kindle browser. Check the user manual for how to do that. You just have to remember to keep calibre runniing on your computer, even in the tray area. Close it completely and the server shuts down as well.
A final caution, if you happen to also have a Kindle Fire, the email function, especially as regards periodicals, simply doesn't work. The stuff gets there, but Amazon messes with the file in transit and it loses all the navigational controls, i.e. no "Sections and Articles." They show up like a book and can't be "browsed Through" like a periodical. The calibre folks have so far been stumped on how to fix that. Seems its an Amazon issue. You also can't access an "archive folder" on the Fire. And access to their famous Cloud doesn't work either, at least not yet. In many respects the Fire is still a cart without a horse.
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