It is pretty easy to get a running system (new install) working out of the box. A Knoppix LiveCD is a great example. Most new Windows installations work well out of the box as well. The problems show up after the systems have been running for a few months. Updates and patches arrive. Some are benign. Some cause significant failures. When the smoothly operating appliance stops working smoothly, it's time to fix it. That's what separates the appliance operator from the competent system administrator. What raises the stakes is that the system that has been running for months now has lots of valuable data and user customized configuration invested in it. Often that data represents significant hours of labor. It's not just a "throw away" and reload proposition. It has to be restored to working without destruction of all of the other investment in the system. That is not a task for an unwashed appliance operator. If you're going to adopt Linux as your OS, you also need to make the commitment to be a competent system administrator to properly maintain your new baby. It's going to take time and probably a fair number of new books on your shelf. "Free" only applies to the initial acquisition cost, not the ongoing maintenance.
When I went from the 2.4 to 2.6 kernel on my desktop, rather than just do an upgrade in place, I opted to reload because the way the /dev/ filesystem was changed in such a major way. Since my /home partition was a separate physical drive, I simply told the installer to ignore the drive while wiping the rest of my stuff. Once it was complete, everything just worked. All my data was exactly where I left it, and all my preferences were maintained. That freaking rocks IMO.