1. Doesn't macOS turn off font antialiasing for retina displays? I believe retina displays (with desktop scaling) is the real solution to crispy fonts.
apple was using grayscale shape-acxurate smoothing, it works on any display with any arrangement of subpixels
windows clear type is using pixel-accurate subpixel smoothing, it works only in one direction with correct subpixel pattern
what people (including me) dislike about windows fonts is aggressive hinting, that is snapping font shape to pixel grid, it made sense in displays around VGA (640x480) but does not make sense on FHD screen
I think what you are used to has a big impact. I use a 22" 1200p screen and still like the aggressive hinting; I've tuned my fontconfig to be more like windows. Mac style rendering just looks fuzzy to me.
As an aside the PPI of my screen isn't that different from the PPI of my 15" CRT running 1024x768 (both are about 100). Note that there was less than 15" of usable space since CRTs were rated based on the tube size, not the visible size.
windows clear type is using pixel-accurate subpixel smoothing, it works only in one direction with correct subpixel pattern
what people (including me) dislike about windows fonts is aggressive hinting, that is snapping font shape to pixel grid, it made sense in displays around VGA (640x480) but does not make sense on FHD screen