I have upgraded both ways on various machines with varying success for either method.
- My main box is multi‑boot. On that box, my main and second partitions have been successfully network upgraded from Precise to Trusty to Bionic and now to Focal. That's 3 LTS upgrades with only minor problems along the way. Nothing that could not be figured out with a little cussedness and the help of fellow forum members.
- The third partition is more experimental: it contains a standard release on LVM for easy snapshots. This one has had bigger problems, sometimes necessitating scratch upgrades. Most network upgrades go well, but not all. Because they are standard releases, the problems do not surprise me.
- Mrs DuckHook's machine and any of half dozen assorted laptops, spare desktops, R-PIs, etc are usually network upgraded with only minor problems.
- I run a half dozen different servers. They are typically network upgraded with few problems. This is also expected since they are much simpler, with no GUIs and stripped down to only the most minimal services. There's simply less that can go wrong.
I suppose I should explain what I mean by "minor problems". I don't consider the following to be a big deal. They just require a bit of tuning or a workaround:
- Broken sound (fixed by nuking old pulseaudio config)
- Dropped printers (fixed with newer hplip database)
- Strange artefacts in DE (fixed by clearing out old caches)
- Poor, stuttering video with dropouts (fixed by changing from Totem to VLC)
Bigger problems have been:
- No video at all (regression in kernel)
- No network (driver dropped from kernel)
- End of 32-bit support (still 2 years of breathing space, but will ultimately be forced to use Debian)
Bigger problems can stump me. Sometimes, as in the case of 32-bit EoL, there's no other option but to drop Ubuntu altogether.
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