My parents are both ~60 y/o and run Ubuntu since roughly 5 years. I gave them a crash course over the course of 3 days and my mother took notes on all the things that she uses daily - spread sheets, word documents, images, browser, Skype etc..
I've set up dynamic DNS and a few other things so I can help them if something goes wrong as we live 12000 km apart. After a year I realized that none of them ever asked me anything. So I asked my dad "Why do you never contact me to help with the computer?". He responded: "Well, everything just runs!".
Before, with Windows, I can't even count the time I've spent fixing their laptop.
I put my parents on Xubuntu about the same time (more of an experiment that I didn't think would work). I showed mom around for 10 minutes, put a few shortcuts on the desktop, told her it was like Windows, and left. They adapted surprisingly well. Issues became few and far between. I'm still surprised the HP printer/scanner works as well as it does (out of the box!).
It turns out that Linux in general is mom-proof, and can handle email, web browsing, and solitare extremely well. Mom loves the gnome-games games; she has always liked Mahjong, and was amazed that there are that many varieties of solitare! I put them on Mint for about two years, but they're back on Xubuntu.
Another bonus, malware and unsolicited "Windows support" calls are largely, if not completely, ineffective.
Hmm, my parents have a Win 7, I set their account to user level and gave a few lessons on security and in the last 4 years I didn't have any complains (except once with the printer which turned out to be because of a bad USB cable), so go figure, I guess you just didn't know how to properly set up a Windows system for basic users.
I've set up dynamic DNS and a few other things so I can help them if something goes wrong as we live 12000 km apart. After a year I realized that none of them ever asked me anything. So I asked my dad "Why do you never contact me to help with the computer?". He responded: "Well, everything just runs!".
Before, with Windows, I can't even count the time I've spent fixing their laptop.