My housemate is a regular user (not power user) and a known potterer. He loves figuring things out and patching things together, and wanted to try a linux desktop, so I set him up with one. He didn't want me to help him out, as he wanted to find things out for himself, to try it without me coming in and 'just fixing it'. I watched him struggle for months, then he admitted defeat and went back to Windows. He still (theatrically) shivers if we discuss the topic.

I've seen this experience is seen in the wider desktop space - the only time a free desktop is suitable for low support usage is when it's so locked down it's not really a proper desktop environment anymore; that locked down, it's more like an appliance. When something goes wrong with a free desktop, it's not just a matter of figuring out what went wrong, but which are the right steps to fix it. This error on Gnome, will this fix I found for Fedora work on Debian? Is the problem in Gnome desktop or in the distro?

My colleague once had a problem with something in Ubuntu, and found that there were four different solutions depending on which of the last four releases were in use. When your changing releases are years apart (Windows) this is less of a problem than when they're 6 months apart. I was pleasantly surprised when I loaded up ubuntu 14.04 and saw that it looked the same as before.

Note that I'm not in the enterprise environment, only that I've had to help a lot of people with changes from OS version to version, and understand the need for stability... which is a reason why the path Win8 took particularly puzzles me, given Microsoft's strong position in the business world. I think that the free desktops are getting there, but haven't quite arrived yet.