Everything I can run on Linux, I do run on Linux. That's left less than a handful of things that still need Windows, none of which need any direct internet access (for the few files that go back and forth, they are transferred twice with one of the Linux desktops as the intermediary). So all the Windows stuff is on one computer still running an old obsolete Windows 98. So obviously I don't need to upgrade every time Microsoft wants me to.

As an old hand at Linux (since 1993) and even doing some development on it, I can't be a good judge of what is or is not user friendly to the average computer user. But I have tried installing some of the pre-packaged Linux "distributions" before with varying levels of success. A friend who actually wrote a book about how to use it recommended one that installed just fine with no need for me to intervene in any way (something I probably too readily do when I shouldn't). His book is about one called "Java Desktop System" from Sun Microsystems. The book at Amazon can be found here:
http://www.amazon.com/gp/product/0596007523/103-1695720-7347815

I personally use a distribution called Slackware, which is the earliest distribution of Linux still available. I like it because it lets me dig in and change it around very easily. But this is probably not for you unless you also like to explore and tinker around with computer software.