Last year she was sick of Windows XP, and Vista seemed even worse to her. So, after making sure her hardware would work well with Ubuntu, we got into a lengthy conversation about the pros and cons of switching and ways she could do self help while making the transition.
After I felt like my due diligence was complete, she decided to take the plunge and asked me to switch her machine to Ubuntu. I was concerned that recovering from trouble might be problematic since she lives so far away, but she said she had a colleague who was "into Ubuntu" who she was sure she ask for more local help if it came up.
She soon returned home, and I quickly forgot that I had switched her. Today, I had reason to drop her an email so I took the opportunity to ask if she was still on Ubuntu and how she was liking it. Her response:
"I am still using Ubuntu. I like it. I couldn't play encoded DVDs at first. I was going to call you or talk to our computer guy at school, but decided to research the issue myself on the community help site. I got it figured out and upgraded to the newest version at the same time. It was really very simple to work through. I'm very happy with it and I absolutely hate going to windows machines now, they suck."
Keep in mind that while she is a very intelligent and independent woman, she is by no means "a computer person", and prior to her conversion had only very limited exposure to Linux.
This just goes to show that with appropriate prep and help through the initial hurdles, non-techies can happily and successfully use Linux. In this case, the only active support she received is the same support that Windows and OSX users take for granted; having their OS installed and configured for them when they take the machine out of the box.