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Longtime Debian user, looking to branch out.
(lemmy.sdf.org)
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Upgrading them should be done frequently since it's a rolling release distro. If you wait a long time and then do a large update, you may run into issues because they are not really designed for that. You should always be on the latest version of packages.
What do you mean? What happens if you leave it too long? How long is too long?
Nothing usually happens but the distro is not tested in that way. The devs don't wait six months and then update every package in the system at once. It probably works (and it has for me, every time) but it's just not what users do normally. They keep it updated all the time.