Q:

How to keep my data during upgrading?

I'm currently still on Ubuntu 8.10 and now wish to upgrade the latest version (14.04 at the time of writing). First of all is it safe to update from such an old version? What problems should I expect to have to deal with?
What's the best way to keep my user preferences and data intact? I specifically want to keep:

Tomboy notes
Firefox scrapbook pages (extension)
Mozilla Evolution email history/address book

A:

Backing up your home directory should be sufficient to keep your personal data.  If for some reason you have please files in other areas on your file system apart from it's defaults, it's something you may have continuously specified, you should back that up also.
Upgrading on Ubuntu is failrly safe.  But it's possible that you can incur some problems from coming back from so far.  I don't think it will take you all the way from 8.10 to 14.0, it'll upgrade you in steps... first to 9.x, 10.x, 11.x etc.  So it will take a while to get up to 14.04.
Before stating your upgrade, try to insure you have the latest updates for the version that you're running by running:
$ sudo apt-get upgrade
$ sudo apt-get update
$ sudo apt-get upgrade

And reboot if the system prompts you.
If the upgrade fails you can always perform a full install, just don't choose the format option.  It'll prompt you that your nomral /etc /bin /sbin (and other system directories) will be removed and recreated.  Your /home directory will not be removed.
By the way, there are significant changes from 8.10 to 14.04 in that many of your configuration preference might not be supported on the new OS.  You might consider starting a fresh home directory and systematically bringing your documents and other personal files from your home directory backup to your new home directory.

