While on holiday I spoke at length with by brother-in-law. He has a semi-technical background, is deeply mis-trustful of Microsoft and is retired so he has time to kill. He should be a good candidate for Free and Open Software, if he can't be converted to some free things, then it's going to be hard to convert an awful lot of anyone else.
He started by reading some PC Magazines, and then he tried some Linux magazines (UK and French publications). He didn't joing his local LUG, which I think was a mistake. Based on the magazines and shop recommendations alone he picked SUSE Pro 8.x, and installed it.
His experiences of this exercise are as follows:
Personally I think his first mistake was not finding someone local to help. He lives in Paris, and I think there are a few Linux/BSD types over there who could have helped, and know enough English to converse with him.
While a boxed distro may be a good idea, I think he picked the wrong one, something with less choice would have suited him a lot better. While unifying KDE and GNOME isn't going to happen in a rush - if at all, that kind of difference is very confusing to new users if not carefully explained...
I think the biggest thing that is required is a significant overhaul in documentation. This has touched a raw nerve both here and on Perlmonks, but a lot of documentation does assume you know what you are doing, and isn't suitable for new users. An obvious problem is that serious users of something, for example Perl, can't always see what a new users finds hard or needs explaining, and new users know what is hard, but don't know the answers.
I'm not saying that Windows is easier than Linux, rather that it has successfully maintained the myth that is easy, by trading lots of things like security and stability off against "apparent ease of use".
As a contrast, a colleage at work tried Knoppix, with some help from me, had no problems and has found that Google knows all. His wife used it, without even realising that it wasn't Windows XP...