how do you figure that?
98% of all configuration is retained, applications do not need to be reinstalled, all your files are where they belong, and it's overall very pain-free if you are tech-savvy enough to do the command line part.
So yes, I would totally rate this as better than upgrading between Windows versions. Even compatible ones like Vista and 7 required much more configuration work afterwards and took longer. Less technical skill required though, but users could just pay someone to do it for them on Linux.
Not sure what it's like to upgrade Mac OS X, I would actually expect the ease of Windows and compatibility like Linux there. I'm kind of curious now.
The main beef I have with upgrading Windows though is the time it takes to do so. A while ago I updated someones PC from XP to 7 and when it restarted after the upgrade it just ran like complete crap. Took at least 3 minutes for the desktop to come to a usable state after it had appeared to be fully loaded. This is an experience I find all to often on windows but almost never on Linux. After installing about 8 hours (yes 8 hours) of updates including quite a few .NET frameworks and restarting multiple times, the computer was finally in a state that I considered "acceptable". Started up fast and was responsive within a few seconds of the desktop loading. I was missing a lot of drivers, but I had the driver disc, they were pretty painless for the most part. The resolution still looked a little funky and I found out I had to install the nvidia driver from the website. Was a pretty decent experience after a pretty awful ordeal.
Regarding the time it takes to upgrade windows, Ubuntu too takes the same time for me. I have a fairly good 12mbps connection but still I have never been able to do an upgrade in less than 6hrs.
Use dpkg/synaptic to backup your installed packages and backup your /home...then commit to the time to going fresh install. If you use LTS releases, you'll only be doing it at most every other year.
IMHO, it is worth the time.
The upgrade itself completed successfully after I disabled them though.