All feels more coherent than anything today. It feels like it was sketched out by a small group of people and executed incredibly well. Meanwhile things today look more disjointed like the product of a lot of design-by-committee.
Susan Kare's 'Chicago' in this rendering hits hard in the nostalgia factor to me a well.
I do agree on all other points :)
They look pretty similar but now that I look it them side by side I see it a bit.
As much as it is the style, it's also that kinda.. not-True-type still-a-bit-pixelated edges look that is the nostalgia factor, I guess.
I have wondered in the years since whether the newer abstractions and UI patterns we find in MacOS and Windows are actually necessary. These days both OSes are trying to be tablet friendly, trying to discourage user-installed/curated software, and trying to promote bundled cloud services, so it's not even clear to me whether the MacOS 9 abstractions are really the correct ones anymore, as evidenced by the many problems with cloud backed file explorer interfaces, synchronization, etc.