What customizations are lost when Ubuntu distro is upgraded?
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Been several years since I attempted an upgrade on Ubuntu (since it's so liable to fail), but presuming it works you should be o.k.
I do full re-installs using a new root partition but a shared /home partition and all the config options are retained. I have to re-install any additional apps, but they work as expected. You should be fine - if the upgrade succeeds.
If I decide to upgrade at that time, are my customizations lost, also add on software lost e.g. Codeweavers Crossover Office, and software running inside Crossover, etc.?
I also always do clean installs of Ubuntu. However, I do know that third party repositories are disabled by default when you upgrade Ubuntu. So any packages that were installed from third party repositories will likely have to added back to your system after the upgrade.
In general, distro upgrades don't touch anything in your $HOME directory, so personal configurations should be conserved. They do however, sometimes install new versions of global configuration files in /etc and other places.
Also, the programs and libraries considered the default may change, but again programs that have been independently installed should be conserved, unless changes to dependencies force something to be uninstalled.
In the end the best advice is to simply pay careful attention to all the changes the upgrade wants to make. Especially take note of what it wants to uninstall. Sometimes it just has to temporarily uninstall a package and you may be able to reinstall it after the upgrade is complete, but you should always be aware that this might not be possible.
This is really true for any kind of update. The main difference is that distribution upgrades have the power to install, change, or uninstall just about anything in order to bring the system up to the specs of the new version. Normal updates, OTOH, are much more limited in what they can do and generally won't uninstall anything important without your express permission.
Ubuntu and other Linux distros have a limited useful life, for example Ubuntu only supports its current release until April 2012.
Ubuntu has a far, far more 'limited life' than other distros. Its all part of the way canonical works. A new release every 6 months, so they stay in the linux news as much as possible. Support dropped after 18 months for all 'normal' (non-LTS) releases, forcing people to update to a newer release. LTS (long term support) releases arent really something you are told about if you go to d/l ubuntu, you have to be 'in the know' or else you just get the newest normal ubuntu release.
Other distros are far better for using long term than ubuntu 'normal' releases. Even the LTS versiosn dont have that long a life.
BTW, the current ubuntu version (11.04) actually works till october 2012-
Just because officially it's not supported that does not mean you can't keep running it. But to your question if you are going to wait until 2012 to update, there will be so many changes (like Unity for ex) that you are far better off in the long run, to backup all your data and do a fresh install.