The problem with the linux evangelists isn't that you're wrong about security, because you're generally not. It's that you're preaching something that is beyond the capabilities of the guy who can't manage to make it past Windows 7 and clearly has limited technical expertise
Ubuntu installs the same as Windows and aside from having to relearn some apps you definitely don't need to crack open a terminal to use it. It was built that way from the get-go and is arguably the friendliest distribution of Linux available. Installing new programs is straightforward. The only learning curve would be WINE but even that is straightforward these days. Saying Ubuntu is difficult to use for a new user is more-or-less equal to saying OS X is difficult for a new user, and aside from some polish the experience is pretty much the same down to Ubuntu supporting double-click debian package installs from the UI.
He never mentioned his technical sophistication nor a lack of it being the reason he does not want to upgrade. I think you're jumping the gun. I'm really not a Linux evangelist (though I daily drive it when I'm not at work) but I don't think you're giving the 15+ year old OS packages enough credit here. Even going back to Ubuntu 8.04.4 I don't ever remember it being that hard to use and the major problem was lack of driver support back then. Ubuntu now has a ton of proprietary drivers shipped with it so the experience is entirely different.
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