I genuinely think it fits right in. Apple always had a good aesthetic, even when everything was beige and rectangular. I did a giant chunk of my school work on Claris Works, before I discovered latex. Happy memories.
That aesthetic was widespread throughout the PC universe in the 90s as well. I remember having a giant clip-art library that came on a whole bunch of CDs, and actually came with a catalog book to leaf through. A lot of it looked like that. Another example is Microsoft's clipart library, (in)famous for its images of the "screen bean" guy.
Mac OS 9 has virtual memory (it uses virtual address translation and it can swap pages to disk), but it still has a single address space that is shared between every application.
This is an issue for SheepShaver (limited to 9.0.4 because 9.1 and up require the MMU as you say), but not QEMU, which emulates the MMU and thus runs 9.2 just fine.
No, after 8.6 the system featured a micro kernel on which the old OS ran atop. I think you could opt in for better stability, but I'm not sure. But most of the OS and apps still ran on the same shared memory space with cooperative multitasking, meaning a single app could (and did) bring the whole system down.
I think you can emulate 9.2 just fine, but it's been a while since I played with this things.