For existing Window users I've found picking the applications before a distro works well. Move them to cross platform apps on Windows for all their major uses, and once everything they use has a Linux version, the change from Windows to Linux is a minor thing to handle.
Personally I've been through a few distros, my most recent ones were Ubuntu, when that decided to make the gui hard work I went to Mint, which still wasn't quite what I wanted. So now I run Sabayon with XFCE and have been happy enough not to change for a couple of years.
As far as the command line complaints, it's a LOT easier to talk someone through doing something when you are just dealing with text. It's simple to make sure the commands they enter are correct and to get accurate feedback on any errors that occur. Trying to talk a novice computer user through a GUI process is often near impossible without the aid of pictures and even then you end up with the occasional clown who has their own ideas about what clicking in a particular box means.