My mother is 81, started using a computer about 15 years ago, first Windows 98, then 2000, XP and now 7. From 98 to XP I always used the same (classic) interface. When moving to 7 I tried to make it as "classic" as possible, but MS messed this up. I don't understand that they have absolutely no clue about older people having troubles moving to new interfaces. Was it so much trouble to keep the classic interface?
I installed Mozilla/Firefox and Eudora from the beginning, removed IE from the desktop. She still uses Eudora (which does not install in 7 if I remember correctly, but you can just copy the install folder from XP and that's all). I tried to install Thunderbird once, but she didn't like the buttons. That was years ago. Now Eudora starts to show signs of age as well, and I'm in doubt what to do. I don't like Thunderbirds layout.
I moved her from Office 2003 to OpenOffice and then LibreOffice without much trouble. I helped her get a new mobile phone recently, and I hate the fact that this phone will probably not be available anymore in three or five years, and then she'll have to get used to a different phone. So I'm going to buy a second one, just in case. Same with de house phone. How difficult can that be? Well it can! So another set that has to be doubled.
When this computer is finished and Windows 7 is done, and there is nothing left but a Windows 8 interface, I'm afraid I have to move her to Linux as well. Then I hope to find an LTS version that stays up to date for five or seven years, with a classic gnome interface or maybe something like mint. My goal is to keep changes as minimal as possible, but in the current world, this is a difficult task.