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How "out of date" is Debian really?
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It's really a vibe. I see people complaining about it all the time about Debian, so I'd expect those people to answer based on their own definition of new/old and talk about problems (or lack of) it's brought them.
So then your original question isn't 'How "out of date" is Debian really?' but 'If you complain that Debian is "out of date", what do you mean?'