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That depends - do you want bug fixes, new functionality, and to be able to use the latest versions of plugins? If so , yes.
If you don't want any of the above, then no. Or you can do what some users do and just update every "now and then" instead of as soon as a new Calibre release comes out.
I really don't understand why so many people get so hung up about half a dozen clicks to install a new Calibre version. I mean, unless you use dial-up modem connections from the middle of nowhere, what on earth is the big deal? A couple of minutes and you are done for another week...
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