I think people just have different tolerances and things they're prepared to accept for comfort and familiarity.
If my computer suddenly decided to use random apps that I've never heard of before and starting housekeeping processes out of the blue, the visual layout kept changing, and the location of things changed or became less convenient, I wouldn't start by saying it works perfectly well.
But if you know what you know and that's that, well then that's that.
All of these things, and worse, are given a huge pass every time there's a debate, in favour of concluding that OSX and any windows OS is "exactly the same" and the only difference is preference,
which makes me think the people concluding are either just happy with their lot because they know it, or they've never used any other OS.
High Sierra introduced a lot of mobile+tablet related features that the majority of pro users probably have no interest in, and that gained it a reputation that people love to regurgitate,
but you have to remember that OSX and MacOS has been the same great operating system, more or less, for many many years now.
They're building on an already great foundation.
MS seems to pretty much throw everything in the bin and try again once in a while which, personally, I find way more off putting than anything else I've heard anyone complain about.
People always tell me you can disable X and configure Y and make it just like it used to be but they never realise that's my point. I want to turn it on and have it just like it used to be.
That IS personal preference. I just like that OSX has been largely the same in terms of layout for about 15 years or whatever.
True to say that Apple as a company are less geared towards their pro customers these days, but the OS has been so solid for so long that I wouldn't care if they were selling lemonade as their main income.
What I have works just as beautifully as ever.
The introduction of this years new modular mac pro will say a lot about their future intentions with the pro market, though. They know they dropped the ball with the 'trash can'.
They're quick to dump old technology and, personally, I like that, but I think dropping PCE-Express was too far or too soon.
In terms of pro features, I'm not sure what's missing? It's got solid disk management with cloning options, an unobtrusive file-level restore system that works, updates that you don't need to down tools (for two hours?) for, great image library management, native browser that's better than most alternatives, mail client, ftp client, messaging, a decent enough starter DAW, video editing, audio file conversion, programming IDE+framework.
There's also only one version of each OS and no specific requirements in terms of hardware so backing up and cloning the entire OS back to a new drive, or moving it to a new computer!, should you ever need to do that, takes something like 20 minutes.
It's actually pretty well kitted out, no?
I've never had to defrag (wouldn't know how), never run an equivalent to disk cleanup, never looked at a loading screen for more than about 10 seconds, never had to maintain startup items, never had to scale back OTT visual effects, I don't have to watch my back for all the auto-ticked bloatware boxes when I "install" something, never had to disable internet for any reason, and although I've run virus scans for giggles I've never found anything.
I also restart, on average, about three times a year.
I agree that it comes down to preference in the sense that someone will always prefer one or other, but I don't think that they're in any way equal.