I'm typically a laggard when it comes to upgrading my OS. I like for things to be stable -- I don't like to waste time fiddling with things unrelated to what I've got to get done for whatever project I'm working on.
So now in July, I'm upgrading to Ubuntu 9.04 (released in April). To state how much of a laggard I usually am, I think this is the most up-to-date I've ever been on an OS upgrade.
I decided to use the standard "upgrade to 9.04" feature exposed in "Update Manager". So when I saw a screen like this:
then I felt happy. I felt like I knew what was going to happen, and that I was in control of the process to some degree. This freed my mind up and let me think about what I could do to minimize any upgrade risk.
In the past, because of the helpless feeling of being out of control of what's going to happen and what I can expect, I've avoided upgrading until the pain became great enough to justify a full backup/reorg of all my files that I for sure wanted to keep.