When I first upgraded my desktop (Yeah I know you’re talking server here) from Ubuntu 7.04 (Gutsy) to 8.10 (Hardy Heron) I has all kinds of issues. I was ready to do the ‘ol nuke ‘n’ pave as I had in the past with Windows upgrades. But I waited, since I was able to use a terminal windows with command line workaround. I am glad I waited. With the most recent updates I have pleasantly discovered 99% of the issue are gone.
SO far, I find Ubuntu is a real challenge to Microsoft, as they are doing such a great job with updating when the community says they have issues. And obviously the price is excellent.