Give Grandma a Windows XP disc, a computer with no OS, and tell her to get it to a working state. It's going to be difficult I think for computer newbies to install and configure operating system regardless of which it is.
You are pretty much like Grandma, maybe a bit more technicial, but if all you have been using is Windows you have no clue how to get things done in Linux. Especially if you have been using Windows for a decade or more, it will take you years to reach parity
in Linux. I've been using Linux nearly fulltime for 2 years and I am still a newb compared to many people, and I know much more about Windows then Linux still.
The difference though is I took more effort to solve the problems I have. Your lucky you even had a video, let alone being able to plug in a second monitor. I've installed Linux on machines where X blew up on my face. I had X blow on my face *on* an installed
system. But I never really said this crap sucks and went back to using Windows exclusively. I figured out what went wrong and I fixed it. Because for me this is a learning expirence and I don't have very much to learn using Windows.
Now I can feel confident enough to go to job interview for "Windows Administrator", or "Linux Administrator". Or "J2EE Developer" or ".NET Developer".
Really the less people that discover Linux the more I can use my expirence to my advantage. So I don't know if all this "Linux needs to overtake Windows" is such a good thing.
In the world of the blind, the one eyed man is king.
I use OS X and Windows 50/50 so I not new to a unix environment and I've been playing around with Linux for years on and off, I've even read a few books on it but just never had time to get properly into it. I understand how to use bash and vi and how certain
things work in Linux so I wouldn't say I'm grandma as you put it .
I could have probably spent another few hours getting it to work, and if I'm honest when I get some time I probably will but why should I have to.
My point is if Linux on the desktop is to be taken seriously people shouldn't have to spend hours in the terminal window messing around with config files.