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So I installed EndeavourOS ...
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Only significant issue that I've had with EndeavourOS/Arch is when I had a laptop with it installed and didn't update for like 6 months because I rarely needed it. When I went to do a full update, it really messed multiple things up. There were just too many massive changes at once. I just shrugged and reinstalled with the newest ISO, but if I had heavily customized it or something, I would have been pretty annoyed. Ever since then I usually install it with BTRFS and auto pacman snapshots.
Also, never perform partial upgrades unless you know what you are doing. That's apparently the fastest way to mess things up. I played with this before and it definitely will break things.
I certainly do recommend keeping a rolling release current.
That said, I have successfully fully upgrades several stale Arch systems. The biggest issue is the out of date GPG and keyring. Once you get through that, it is generally cake.