However now that I looked into CentOS, I find myself at a point where it's transitting to a major new version. So the key question for me is, should I wait for CentOS 5 to be released or just go for 4.4?
I guess it depends on how conservative you are.
With 2 servers currently running CentOS 4.4, my plan is this: CentOS 4.5, followed by 5.1.