I don't know what it is like on Debian, but for instance, upgrading from Centos 6 to Centos 7 is clearly NOT recommended, because, given that one probably keeps one's current system up to date, the packages of Centos 7 are older, and so one will have to deal with all sorts of conflicts between packages. I've heard some people have done it, but it's really not worth the effort, as it's very difficult. I suppose the same scenario goes for the Debian upgrade.
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