I haven't done a lot with Debian based systems -- I've traditionally been a Slackware / DIY / Redhat person. I just looked through the documentation and a bit of the source code for apt-get, and nothing popped out at me for a rollback feature. If I come across anything I'll update this comment for you.

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.