What does 'watering down' even mean? Why is 'user friendliness' bad? Do you want computers that are harder to use for some reason? If that was the case why don't you also give up your favorite OS or interface or language and go back to carting around stacks of punch-cards or flipping physical switches to set memory registers? Or are you just trying to make yourself feel superior as a technically-minded person?
Also, I dunno if you know this, but people interact with health and legal shit all the time, that's why there are people who only do that job. Reading some email and punching some numbers into an excel sheet are about the equivalent of signing a lease or getting a flu shot. It's not their job to know how things work behind the scenes, just like it's not your job to know how to make vaccines or write legally binding contracts.
And finally, you're forgetting two important facts.
- Older people tend to have been in their jobs longer, and at higher levels where their computer expertise matters less and less
- Companies, especially in certain industries, don't update their hardware/software as often as IT would like them to
So that old guy you think ought to be able to know what a start button is might have never seen one because the only computers they use at work are old SPARCstations from the early 2000s, or might've worked in a bank for the last 50 years that is still using AS/400s from the late 80s or whatever; those machines can't even run windows. You tell me, what are the keyboard shortcuts for copy and paste on a DEC Alpha? Where's the power button on an SGI Onyx? I worked IT in a hospital in the late 90s that was still using computers from the early 70s and shit, it happens way more often than you think.