As an honest answer, I'd say the issue is that MS
- cares too much about legacy
- exposes legacy too clearly
- hides what should be obvious, and exposes what should be hidden.
For example, OSX has a fairly clearly named Disk Utility app with fairly clearly exposed buttons for things like First Aid and Erase.
The equivalent on Windows is the Computer Management app (which is already somewhat problematic because the relationship between "Computer Management" and the "Add Hardware" bits of Control Panel is not at all clear. When you go to the Storage section of Computer management and look around you don't see anything that seems to correspond to a task you might care about (like erasing a disk or checking/fixing the file system) but you see a whole lot of buttons relevant to changing how the program looks (WTF? why is it important to have two buttons for changing the appearance of an already overly complicated program?), and the Action menu only offers to help you create VHDs [but provides a whole lot more ways to lay out the program --- honestly the program seems more interested in ways you can customize its appearance than in any actual computer management}.
But oh, in Windows, you don't actually use EITHER the Control Panel HW section OR the Computer Management app, instead you go to Windows Explorer, select the drive, right click, choose Properties, then in the dialog that comes up find the Tab named Tools.
The point is, all this makes a kind of vague sense if you have been part of the Windows world for 20 years, but it doesn't make sense to a novice. The way functionality (in particular system management functionality) is split across apps and various panels/dialogs reflects history and the addition of new features at different times; it does not reflect a "from the ground up" DESIGN of how to present this functionality, especially bearing in mind the common tasks that users care about.
Apple has been very willing to rethink this sort of workflow design over and over again. Obviously from MacOS to OSX was a big change, then there have been big changes in various apps over the years, just in 10.11 Disk Utility got something of a redesign. MS in the past was terrified to do this sort of large change, and when they finally did (with Windows 8) they made something of a clusterfsck of it, leaving out important functionality, often caring about appearance over usability, and generally enacting a parody of Mac design, a cargo cult that assumed the magic was all in the pixels and that didn't realize the magic is in
(a) asking what the IMPORTANT work flows are,
(b) testing your assumptions against reality and
(c) fixing when your assumptions are proved wrong.
Networking on Windows is the same sort of godawful mess. What ARE Homegroups? What problem do they solve? Why when I go more than one level deep in any network dialog do I start seeing these network terms from the 1980s -- NetBIOS and BEUI and a full tree of every driver that's running my network connection?
Again sure, this stuff is necessary for some purpose --- have it available for those who need it, but don't mix it up with the material that's required by your basic user just trying to get basic internet working.
MS does a little better with say Win7 than with XP, but once again they're frightened to actually rethink and utterly redesign the full work flow, so we get band aids on a messy system, not a clean UI design.
Meanwhile Apple is constantly trying to simplify the user view of this stuff. The full power is there, if you want to launch a command-line or root around inside the Utilities folder; but Apple tries to hide what most people don't need. So, for example, a few OS revisions ago they started to hide the ~/Library folder, presumably because
- almost no-one actually needs to interact with it and
- those who did interact with it tended to screw things up.
(~/Library is full of stuff that looks like you don't need it. Per user prefs, per user caches, log files, and basically every "technical" file that an app needs but that is not a user created document.) You can still open the folder if you believe you need to, from the command-line, but Apple has ensured that the ignorant cannot shoot themselves in the foot.
Similarly they started a few revs ago to largely present in Finder a file system that appears rooted in your home folder. You can break out of that to see the higher levels of the file system but once again you have to work to do that, and Apple's belief (one I'd agree with, based on how I've seen family use their Macs) is that most users do not NEED to know that there is anything on their hard drives beyond their personal home directory, and allowing them to explore there just causes trouble.
You could argue that Windows tries to do the same thing in Windows Explorer, and they tried to do it before Apple, presenting eg the Libraries section of the sidebar. But in my opinion (I think validated by IBM's experience) once again they did the job half-heartedly and instead of constant iteration and improvement, they made one set of changes and then appeared to lose interest. With Apple you see a pattern where, pretty much every rev of OSX from 10.0 has worked harder and harder to hide the dangerous parts of the file system from the user (and to prevent them from HAVING to interact with those dangerous parts). On Windows you don't see that CONSTANT attempt at improvement and the removal of problem areas.