Did you actually try to get someone older to use the swipe gestures that are mandatory on new iPhones? Many of them can't be disabled even through a11y or provisioning options and constantly frustrate.

Another massive issue is that iOS doesn't really mark clickable elements / buttons anymore - after iOS7 redesign it's really hard for people to recognize what's a tappable element. Especially since a lot of apps now have their own UI design language.

You don't notice these things until you try to teach someone non-tech savvy. Then you notice just how inconsistent and horrible to use the new OSes are. Even Apple ones.

> What challenges did you face with them and iPhone?

  - Difficulty typing on the tiny SE screen
  - Can't send text messages from the computer (no Messages on Chromebook)
  - Accidentally muting contacts all the time, so missing calls
  - Butt dialing all the time
  - Not being able to get back to the phone screen to find the speaker button and other basic ui functions were not intuitive
  - Spanning multiple ecosystems is a recipe for confusion (Apple photos vs Google photos, for example), and if you have to choose one Google wins (youtube, docs, chromecast, etc, etc).
  - Tons of text spam

Going all-in on Apple (iPad instead of Chromebook) would make some of these better, but still worse overall imo. Just look at the iPhone SE next to the basic Pixel A, the SE looks like a tiny antique (the bezel really hurts).