As a long time Debian (and Ubuntu more recently) user, I've been using
`apt-get dist-upgrade` for nearly a decade. I've never had a problem
with it. I have 3 servers in my garage that started as Ubuntu 5.04
systems, they now run 9.04.. all upgrades after the first install. My
desktop system at work started as a 7.04 system several years ago, it
now runs 9.04, upgraded it twice with no issues.
I gotta think you're not doing something right when you upgrade. I
just don't have the problems you describe. And using your own words..
even if you do have an issue, taking half a day to fix it still beats
taking a whole day reinstalling from scratch.
I just couldn't imagine reinstalling every system I own or use
everytime a new version was released.