Apple's claim to fame was always that "grannies and other tech illiterates" could use their stuff without having to go to any help resource. Apple has lost its advantage there. Good luck getting many of them to talk to their phones.

For example, my wife, my daughter, and my sister are all really smart but not tech savvy. They love Apple, but the "upgrade" to iOS 11 is bothering them quite a bit. (Too bad Android isn't any better.)

My mom is still on Windows. She hates Windows 10 and really misses XP, but she can get by OK without too much help. She's 84. I'm thankful she never went to Apple, frankly. She would never talk to a computer. That is in the ridiculous range for her.

You cite Office 2000 as an example of bad UI but honestly it's far easier to find stuff in menus if you're not sure where it is the having to hunt through the Ribbon bar for an icon that looks vaguely right to what you want. And sometimes the Ribbon bar just hides stuff completely if the Window isn't wide enough.

The thing with menu driven interfaces is while they're ugly, they do make functions discoverable. You don't need to remember what icon you want nor where it is, you just need to remember it is in the menu.

From a personal perspective, I still find myself hunting for common functions in Office even after years of using the Ribbon bar. I've found that to be the single handed biggest productivity killer to Office

Overcast is a great app. Smart Speed is awesome, syncing between devices works perfectly - something Apple hasn't gotten right in 6 years -, playlists are logical, and it works better with the Bluetooth controls in my car.

I when with Pocketcasts. For one thing, they haven’t explicitly said they don’t want my money, like Marco Arment has said. For another thing, i like the interface better.