I'd prefer Android on my Chromebook Pixel (assuming for a second that I didn't just install Arch Linux on it) instead of having Chrome OS. I'd take a working Skype + Browser over just a Browser. There aren't any webapps that I really use that don't have a comparable in quality or better app. Assuming multi-window works, this would actually just be ChromeOS++ for me.
They also get lost in the GUI in my experience. Too many things that are clickable or possibly clickable, too much information on the page and they get overwhelmed.
With CLI, you do have to remember commands and compose things, but somehow it is easier for them. I am actually always surprised by this. More people should try to teach their older relatives some CLI magic.