Comment SoftShell (Score 1) 823
My grandma has had amazing success with SoftShell. Basic email, photos, games and very simple web browsing (e.g. no scroll bars, pop-ups, etc). It is for Windows and can be configured to run when the computer starts, so she never has to see any of the Windows interface like auto-updates, etc...
We combined it with an HP Touchsmart ($1100) touch screen computer and it's so friggin' simple with the touchscreen (i.e. touch the 'mail' button to read new email, done) that she learned it in 5 minutes. You can also add people to her address book and add bookmarks remotely, which is nice...