Many of the problems are likely really hard to fix because there doesn't seem to be any rhyme or reason to them.

Apple always seem to prefer adding in a shiny new feature than fixing something that doesn't work. But I do fear its foundations are too wobbly for it to ever be more than a frustrating, buggy mess. VoiceOver on the Mac seems to have all the ingredients to be an amazing screen reader. Currently, I'd not consider switching back to Windows. For me, the braille experience with Ventura is really smooth and I love the upgrade. Since Monterey, they're constantly fixing issues concerning Braille, especially in the single item mode. Just a disclaimer, I'm mostly a braille-only user. In my case, I'm doing more on my Mac than I've ever done on my Windows machine. VoiceOver even speaks in the safe mode and even if you have only the base system installed (So, no macOS volume group) and I can boot from different volumes without sighted help needed. For example, I can delete my boot volume and reinstall the Mac completely blind with VoiceOver. Also, for me, I find that I get much deeper and consistent access to the system with a Screenreader than it's possible under Windows. Under macOS, I can navigate through the window of an application in a logic structure. With JAWS, for example, I had to tab around every time until I find what I was searching for. I find that things are working more consistently than they do under Windows. The mac gives me the most convincing experience I ever had with a computer. Almost two years ago, I switched from Windows to an M1 machine.

Windows vs mac vs linux user friendly