For people with >2 servers, that might be the right solution, but for the others, scripting deployment might be just more overhead.
Oh, and there is another upgrade trick (I'll have to see if I still have my old writeup on it, and post it as a Gist). You can query the package manager, and make a few lists. First, list the packages (and versions) that are installed. Secondly, get a list of any file owned by a package that has changed since package installation (compare the file MD5 sum to the package's record of same). This should be a small list of files (mostly configuration related) that can be backed up. This gives you a good way to roll back changes if needed, and keep a system documented.
Finally, with Yum, you can roll back updates. Take a look at "yum history", and "yum history undo". This has saved me a couple times.
Do you know, if this rollback stuff is also available for Debian based systems? Sounds pretty good. I regret, I don't know yum, it is for RPM-based systems, I know, but the last systems I used where all Ubuntu and Debian.
But I know what you mean about hating the sysadmin side of things. Of course there are people that really love it too -- there's sort of a mindset that you have to get into, just like with development. Maybe this could be an idea for a new service -- matching up programmers with side projects, with sysadmins that are looking for side projects to help manage.
That sounds like a fantastic idea. Even in my case, I do "OK" as a sysadmin most of the time, but would love some occasional guidance or assistance.
And I lack the time to really dive into automation stuff and that sort. So many interesting tools are available, but you always have to take time and learn it first.
Over half the servers I admin are running some flavor of Debian, and have for at least five years or so. To the best of my knowledge there's no rollback method for Debian updates, short of relying on filesystem tricks like using ZFS, discussed upthread.