Drove a 1968 Town and Country Squire Woody Station wagon until he passed away in 1987. It worked for him. Good for him.

But in business, there becomes a supportability factor. I've seen one practice that still has an IBM PS/2 doing daily tasks that are practice critical - on Windows 3.11. They've got no alternative when something finally breaks - and the app they are running won't run on anything they'll be able to find today. They're going to have to hit Goodwill and pray when they have a problem.