Which OS is better, Windows, Mac OS X, or Linux?

Note: someone merged this question now including Linux as well; my answer relates to Windows and macOS only, pertaining to the original question.
(Updated in March 2017, using macOS Sierra 10.12.4 beta and Windows 10 Pro Anniversary Update)

tl;dr
If you’re a gamer, you’ll have to use Windows.
If you’re working in an office network environment, don’t even bother, Windows is theonly relevant option to consider.
macOS has some features that Windows does not have (or pales in comparison) that make it a better option for a single user environment - if you actually know you’ll use those features. In any other case there are no significant differences and applications for every major work activity are available for both systems; do consider though that Microsoft is probably developing a better ecosystem and interaction with multiple devices and platforms than Apple is.
(update since previous edit in June 2016: no significant changes, though Microsoft keeps improving Windows on the desktop at larger strides than Apple is with macOS. The one critical handicap for Microsoft is still the wide lack of support for the Windows Phone platform, from which the gap to iOS is immense and not getting smaller.)

I’ve used Windows in a corporate office environment for years (up to Windows 7) as regular user. Today I have deployed and have been managing Windows 10 clients in a fairly small Windows Server domain office infrastructure.
macOS has been my home and personal business OS for the last 7–8 years, and before then I’ve always used Windows as a relatively savvy power user.
Back on point - everyone's answer will be different, but here are my key points for both systems (mostly UX). Sorry for not being too organised.

Price - Winner: macOS
  • Windows is usually free if you buy it with a new computer, though it’s usually the Home version (which has some limitations compared to Pro, including not being able to change the display language).
  • Windows 10 upgrade from 7, 8 or 8.1 was made available for free for a significant period. Upcoming major version updates are expected to be free, probably in the same fashion, but that remains to be seen.
  • OS X has virtually been free for a long time now (maybe since Lion?), and updates are expected to remain free as well.

File Management - Winner: Windows (but macOS Quick Look is brilliant)
  • Explorer is much easier to handle in Windows than Finder is in macOS. Even if the user is not savvy it is possible to be fairly soon using keyboard shortcuts and enhancing workflow.
  • Copying and Pasting files with your keyboard only is very simple on Windows. In fact, almost everything is easier, more logical and faster to do in Windows Explorer than with Finder, especially if you use the keyboard a lot. Using a mouse will still be better with Windows, but using a trackpad you’ll find some operations to be easier with a Mac.
  • macOS Finder renaming features are far easier and powerful to use than Windows’;
  • The single most important feature in Finderin comparison to Windows Explorer, is Quick Look. It’s impressively useful, for a ton of reasons: if you have a file selected OS-wide, just press the spacebar (which serves no other purpose OS-wide except when typing a space) and you get a preview of a document across workspaces, quickly preview an image before selecting it on an Open dialog box, press ALT to zoom in and move around, etc. I know you have that preview pane in Explorer but it’s not even in the same galaxy. Quick Look is awesome and the fundamental macOS Finder killer feature.
  • I also like the fact that the context menu selection options vary by changing the keyboard selector in macOS, but this is a minor feature.
  • Customising folder/alias icons with macOS is not easy, where possible at all.
  • You can rename any document file, open or not, in a lot of macOS applications, including from the title bar. In Windows you can't, and “file is open” issues arise frequently.
  • Oh, and the 260 character limit with Windows [thanks for the correction, including the information that this should be no longer be an issue with the last major iteration of Windows 10. Update in March/2017: this has improved but it is still not eradicated]… I’m skipping more on this because it gives me headaches and can drive one to insanity.
  • Disconnecting external devices (usb drives, etc) is far easier with macOS

Search/AI Assistant - Winner: macOS
  • Note that I do not use Cortana on Windows and only partially on macOS, due to not being available in my location and/or language (European Portuguese). I use Siri for some CarPlay tasks in Brazilian Portuguese but its advantages are very limited in this context.
  • CMD+Spacebar to activate Spotlight search is an impeccably useful tool, another killer feature of OS X which works without using Siri, a strong advantage compared to Microsoft’s search. In essence you have three “search layers” in macOS and two on Windows:
    • macOS: 1) file search, 2) “simple power tools” and 3) full AI
    • Windows: 1) file search, 2) full AI
  • Here’s the thing about these “simple power tools” of Finder:
    • Someone asks me for a friend’s phone number, I press CMD+Spacebar, type the name, select and copy the result; literally 3 seconds at most. On Windows I don’t think you can do anything remotely similar.
    • Type “100 USD” and it instantly outputs the exchange value in EUR, GBP, etc.
    • Type “100+20/20” and it will output … 101
    • Type any single word and the dictionary will also be suggested as a search entry
    • And more.
  • Windows Search… Well, to be fair: if you’re using it on Explorer it works very well. Other than that I have to say that I have yet to read something useful actually being output from the Start Search panel other than Control Panel settings and Apps, but again, my location does not support Cortana (update on March 2017: still the same, sadly). In this respect, Finder’s search also works very well.
  • Automatic file searches work relatively well in both systems.
  • The Dictionary features of Finder are awesome (including three-finger tapping a word to get a popup with its meaning, almost OS-wide). I have several languages active and use this all the time:

Window/Workspace Management - Winner: tie, depends
  • Windows 10 has the Start Screen or Start Menu. Many don’t like it or actually learned to hate the Windows 8 iterations. I like it. I also like Metro Apps in general because they streamline information in very simple and easy to use applications. It was crucial to have these co-inhabiting the desktop with other windows, Windows 10 made this right. macOS has nothing comparable (it has that iOS apps layout that no one uses and serves no purpose).
  • Notifications: Windows 10 and OS X 10.11 both have similar notification sliding side bars. Windows 10 is simpler and a lot more useful given it has some quick settings buttons (particularly useful in touch screens) and it has one pane only. Why does macOS have two sidebar panes you have to switch between each other with a button? Why don’t the sidebars extend in width if the user wanted!?! It they would I guess they could be more useful.
  • Windows window snaps and keyboard shortcuts are really useful and quick to use for e.g. working with documents side-by-side. I use Spectacle (3rd party app) on my Mac to achieve somewhat the same. With El Capitan you have something similar but only for full screen apps. Update on March 2017: using Spectacle on macOS is very good, though Windows 10 still offers some nifty features with its snaps.
  • I feel Windows’ windows are slightly quicker to handle around the current desktop than Mac OS X, especially if you are a power user and have been using it for some time.
  • Windows open applications management is probably better productivity-wise, because you can find your windows very fast. But macOS's window management is dramatically *different*, with Mission Control and multiple work screens being a huge win for Mac OS X.
  • To reinforce the last point: Mission Control (multiple desktops management) is one additional stellar feature of macOS because of how easy is it is to move windows across desktops, switch desktops with the trackpad, but it can quickly result in a productivity loss. I sometimes end up going back in forth looking for an open window app.
  • Windows tab cycle through all window options works a lot better than on macOS and is very, very useful for power users. Note that this is referring ALT+TAB, not CMD+Tab vs Win Key+Tab.
  • macOS's screen capture tool's *shortcuts* beat the similar Snipping Tool and shortcuts available in Windows. Very, very handy and much, much better in macOS. Here’s two window snaps (Shift+CMD+4 > Space bar) of Mission Control in multiple screens:

General Applications - Winner: tie, depends:
  • The experience of using Office is still better on Windows that on macOSbut there is no other software for either platform that can do any better for most applications. I wrote in past edits for this answer that Microsoft was improving Office on macOS and it did - a lot. I can now use Office for Mac for almost 99% of what I do, which is awesome.
  • One exception to the last paragraph is macOS’s Keynote, which is a lot better than Powerpoint, which I do not use. Edit: “better” is probably an inadequate term to use in this case; Keynote is simpler and more streamlined across [Apple] devices than Powerpoint, but the latter probably does a lot more (if you need that).
  • On Office for Mac Outlook:
    • It’s actually insane that if you have your information mainly stored in iCloud you can’t use it with Outlook for Mac but you can with Outlook for Windows (via the proprietary Apple iCloud connector). You can connect via IMAP to the e-mail account but that’s it, no contacts, notes, calendar. This remains the same to this date, but it will be irrelevant to me considering (the next paragraph)
    • Microsoft’s http://outlook.com Exchange ActiveSync integration is now fully supported by Outlook for Mac, something that has allowed me to completely ditch macOS Mail, thankfully. Outlook has some caveats, but Mail is just bad.
  • There are persistent glitches with copying/pasting within Office apps for Mac. It’s stressful at times.
  • Mac Mail app is awful. If you want a simple e-mail client app, Windows 10 Mail app is far more streamlined. It doesn’t do as much, but it does well what it can do. With Mac Mail everything seems a mess, especially if you’re used to work with Outlook in an Exchange environment.
  • Windows has this idiotic concept of People (Contacts) / Calendar / and whatnot that are in no way linked to Outlook. You need to setup your Microsoft account in Outlook if you want to access that data.
  • The upper hand that macOS had a few years ago with graphical design and multimedia editing software is currently non existent. All significant tools and apps are available on both systems and perform mostly the same way. Two examples of exceptions are CorelDraw on Windows and Final Cut Pro on macOS.
  • You can do mostly everything on Windows that you can do with a Mac, though the opposite is not true, especially in a corporate environment, with specific software. Other than that it's just a matter of being used to the special features on each system to take advantage when using an application.
  • I find macOS better for writing - much better keyboard shortcuts to move around text, embedded dictionary support across the entire OS, and even its typography app helps.

Gaming - Winner: Windows;
  • I’m not a gamer for many years now, but I do know this isn’t even a competition.

Networking - Winner: Windows;
  • Mac OS X networking is very bad when compared with Windows. Why, oh why can't I have network shares just stick to where they should be!?! Again, working in a networked environment is easier on Windows. I do use my Mac at home to connect to a Synology NAS, and it's a pain. Update on March 2017: this has become better since Apple silently started using SMB 3 instead of AFP, but file share handling is still stupid.
  • I can’t say anything good about macOS on this regard. I’m sure there’s something but I just don’t want to hear it.
  • Ok, maybe AirPlay and Bonjour stuff, but this is not “networking”, it’s more of a device ecosystem. See the next section for more…

Across Devices / Eco-system: Winner: macOS, depends
  • If, like myself, you’re deep in the Apple ecosystem, you’ll find the integration across devices to be very cool - if it works properly. AirPlay works well if your network is working well, AirDrop works when it wants…
  • Update on March 2017 on the last paragraph: this is still true although these issues I mentioned have become less relevant and less frequent.
  • Overall, this is something that Windows is lagging well behind, as I’m using tvOS (Apple TV 4), carPlay (Pioneer SPH-DA120) and watchOS (Apple Watch 1), beside iOS on iPhone and iPad mini.
  • Side note: as limited (and buggy) as it is, CarPlay is awesome and Microsoft has nothing like it to offer.
  • I do not use iCloud for cloud storage, except for iOS backups and contacts, calendar. But since Exchance ActiveSync was made available of my outlook.com account, I’m use iCloud only because I have yet to move all my data from there, which I definitely will. There is little advantage in using iCloud when compared to OneDrive+Outlook.com, even if you’re “deep” in the Apple eco-system, with the particular exception of paying for iCloud storage for Photos (which I also don’t use).
  • That said, the fact that I can use my Surface 3 Pro seamlessly to work on whatever I want to work with (considering files and cloud data), makes this a good sign that when the integration is Cloud based, you can use pretty much anything.
Hardware - Winner: tie, depends;
Hardware is a really tough thing to review, but there are some specific OS hardware functionality that stand out:
  • macOS wins a gazillion points with Mac's trackpad functionality. There is simply nothing like it. Simply put: when I used Windows only, I did not use the trackpad, a mouse was compulsory. Right now, I find myself doing quick retouching on Photoshop using my trackpad. Swiping four fingers between work desktops is brilliant. Four fingers up and all your browser windows are visible across desktops. Surface 3 Pro trackpad's on Windows 10 caused some stir and made many other good options appear, though it's not an as refined experience.
  • Microsoft is - from my p.o.v. - on the right track with the Surface. It’s what I take with me for quick meetings and while traveling, and it’s awesome. I like the overall format and the pen functionality is excellent. Update on March 2017: still true - I use my Surface 3 Pro for most of my work outside the office and it’s great. My previous favourite computer ever was the MacBook Air but the Surface 3 Pro and later are much, much better devices overall. The Surface is very well designed but it’s tough to beat the looks of the MBA.
  • Multiple monitor management has become comparable with Windows 10, though it’s more convenient on macOS
  • High resolution monitors work very well in macOS. On Windows it’s still fiddly, especially with third party applications, though much better than previous OS iterations. If you use 2x resolution on Windows you’ll be mostly ok, but it’s far from perfect.
  • Phone integration in macOS Yosemite (and later versions) is very cool, though phone calls do not work properly when I'm using my Mac connected to the Thunderbolt Apple Display, the microphones get crazy. I would use this a lot more but I don’t because of this. iMessage integration is well implemented though and works great. I can’t comment on Windows, but I’m thinking it will be comparable.
  • Update on March 2017: Mac hardware has been losing ground with creatives on their flagship product (MacBook Pro line) because of their underperforming power when compared to current PC alternatives. There was a time when a Mac could theoretically be either more or less powerful but at the same time built to “just work better”, but Windows’ increasing stability and performance with even more powerful PC hardware made that less of a certainty.

Misc Tools and Features
  • Bash: those who use it will value macOS, but Windows does offer support for Bash as well (I haven’t tried this though);
  • Font viewer: OS X’s Font Catalog is an awesome tool for viewing and organising Fonts. It’s not comparable to Windows’ Character map because that serves a different purpose. But in the end, Windows is losing for not having a tool for *viewing* and organising fonts.
  • Hourly time voice announcements is a pretty nifty feature in OS X that help me keep track of time.
  • TimeMachine backups work very well (in my case using a Synology NAS) and restores work great. I think Windows is a lot better than it was with full restore backups, but don’t have the restore experience to comment.
  • File Synchronicity: I use OneDrive in all my devices, Windows, OS X, iOS and works awesome (update on March 2017: it gets better and better overtime, I can’t stop recommending OneDrive for cloud storage). I particularly like the Photos app in Windows 10 which browses all your OneDrive photos without being necessary to download them.
  • Automator (macOS): Windows has nothing of comparable to this, and it’s a very powerful way of customising macOS.

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