I do wish, however, that they'd include an option with new operating systems to make the user interface look virtually identical to the old one. I'm the help desk for my 83 year old father, whose first experience with a computer was when I bought him a WindowsMe-loaded one when he was 78. I do not relish the thought of switching his computer to a newer operating system . . .
WinXP does have the option of looking darn close to Windows 98SE. It's under Display Properties>Appearance>Windows and buttons. Choose "Windows Classic style" and you're all set.
Set the control panel display to - Display Properties: Themes: Windows Classic
I've never actually compared it functionally to WinMe, but it does look pretty much the same.
I would not. There is no imperative to upgrade him so long as the system is working. Just because MS drops support does not mean that the computer stops working or that crackers are going to start producing malware for his platform. In fact, right now, he is probably safer than many XP users. In this instance, security by obscurity DOES work. Nobody is going to develop a new virus for ME.