Well, that was fun. The upgrade crashed halfway through. I rebooted in recovery mode, finished the upgrade using the dpkg repair option, and then restarted a few times and found that it still wasn't working. Looked like a video problem, so I checked /etc/X11 and found the xorg.conf files had been backed up and not replaced. A comment in the last one inspired me to run nvidia-xconfig and it worked fine. Pretty typical when you use Nvidia drivers, and still a lot less painful than upgrading Windows XP to 7.
Did you install the nvidia drivers using a binary or from the repositories ? If you have installed drivers using a binary installer, it is pretty much a given that you will break things during upgrade. This is because the system has no idea that you installed software from outside its repository.
Not the OP, but I just happened to upgrade from Linux Mint 15 to 16 yesterday (which is not officially supported). Also had some trouble that I needed to solve from the command line (or a live boot), but the upgrade was done in about 50 minutes, everything included.
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.
I can't speak for them, but I think a lot of people upgrading from XP to 7 are going to have to upgrade hardware for it to even be worth it unless you were already on a fairly high end XP box. I think 7 can be optimized to run on lower end hardware, but it takes a lot of work.
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.
Ohhh!!! I din't even know you could upgrade XP to 7!
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.
I haven't used upgrades in a while. Preserve your package list, reinstall / leaving /home untouched and it usually ends up better once you clean up package changes.
I had a problem upgrading to the beta a few weeks ago. I had some conflicting/broken packages and the installation couldn't finish. It seems the WM crashed and I was unable to access a terminal until I remembered I could switch to a tty. Ran `apt-get -f install` and fixed everything. Haven't had an issue on the official release yet though.
I know upgrades are supposed to work, but they almost never go 100% percent right.
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.
I've had very good luck lately simply adjusting my sources file and typing apt-get dist-upgrade lately - though this is using Mint as the base distro (which in turn uses Ubuntu too).