It's stuff like this that makes so hard to onboard new non-techie users. The proverbial mom or grandma, whose knowledge about the "filesystem" and "directory hierarchies" is already pretty weak, would probably spend 30 minutes or more with this exercise in frustration, before giving up and/or grabbing the phone to ask for help.

When you're past the stage of first impressions, it's a death by a thousand cuts.

Windows is not better in lots of these details, but at least users already know its tricks due to Microsoft's years of desktop dominance. I'd argue the effort of changing platforms should be about improving the experience, not about swapping a list of UX issues with a set of different ones, otherwise the change isn't really worth it for most users.

EDIT: oops I meant to write this comment as a reply to the sibling that talks about how difficult it is to select a parent directory in the file picker dialog (https://news.ycombinator.com/item?id=25721368)