Upgrading ubuntu version "the regular way" - does it work?

[yedidel]

After another very hard upgrade from Kubuntu 16 to 18 yesterday... I have to ask.
Does anyone have any positive experience with upgrading ubuntu straightforward? sudo do-dist-upgrade?

I work with ubuntu for 10 years, ubuntu or kubuntu. Installing a new version using a live cd (in case you have your /home partition seperate) always works good.
However, from time to time I try to upgrade and not re-install, and always there are issues. This time for example I had to reinstall plasma since I had white screen of death and also all network drivers since I had no WIFI after upgrade.

I think this is a major blocker from expanding Ubuntu use, and I am interested to know if I am doing something wrong or its just like this...

[Frogs Hair]

I view the regular way of upgrading as a prompt from the update manger and the command line as a manual upgrade. I have upgraded to the next available version when promoted by the update manger and from the terminal , but not from LTS to LTS . There are many changes in two years so I would preform a clean installation in that case.

[Impavidus]

It depends on many things. How clean your system is, your hardware, the phase of the moon...

I've done many release upgrades (both to the next release and LTS to LTS) and they always work, but there are also users (even very experienced users) for whom those upgrades never work.

[CatKiller]

I've done many upgrades-in-place. It's generally been fine: certainly nothing so broken as to demand an immediate reinstall. There have been some fiddly bits - not having a display after an upgrade might be the kind of thing that would trouble a new user, for example - but no more broken than the kind of thing I've done myself through experimentation.

I think the longest chain I've done is around four consecutive upgrades. It helps if you know the big changes between versions in advance, I think. It's generally new hardware that means that I take the trouble to reinstall.

A fresh install is quicker and more likely to work first time. An upgrade is easier and means that you don't have to use your backups or remember that tweak you did two years ago. There are pros and cons to each.