When replacing your Windows 7 PC: Should you switch to Windows 10 -- or a Mac?

If you're going to make a big operating system jump, should you stick with Windows, or move over to the Mac? David Gewirtz details the factors to consider.
Written by David Gewirtz, Senior Contributing Editor

As any Windows 7 user can tell you, Microsoft is getting more and more aggressive in pushing upgrades to Windows 10 from within Windows 7. Some of you may take advantage of the free upgrade, and some of you may be running on machines that don't support Windows 10 -- so you might opt to stay with Windows 7.

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But what about those users for whom it's time to get a new machine? With the exception of some existing contracts or old inventory, you're pretty much faced with the choice of not only a new machine, but a new OS -- Windows 10. Given that you're going to make a big operating system jump, should you stick with Windows, or move over to the Mac?

From a pricing point of view, this isn't as far-fetched as it might initially seem. High end Windows-based ultrabooks are priced near (or even above) similarly equipped MacBooks and MacBook Pro machines.

Take, for example, the spiffy new Microsoft Surface Book. With a Core i5 (Microsoft doesn't specify processor speed!), 256GB storage, and 8GB of RAM, you're talking $1,899. A MacBook Pro with a 2.7Ghz i5 with the same storage and RAM is $1,499.

Sure, there are cheaper Windows machines, but if you shop for brand-name suppliers, the dollar difference isn't much (or may even give Apple an advantage). For the purpose of our discussion in this article, then, we'll skip any more discussion of machine price and move on to the other factors that should factor into your decision-making.

UI differences

A Windows 7 user jumping from Windows 7 to Windows 8 would be far more confused than that same user moving to a Mac. That's because Windows 8 was a completely perplexing change without any visual cues about how the OS worked -- or where the stuff everyone was used to disappeared to.

While the Mac didn't have a Start menu in the lower left of the screen, the menu is visible and prominent, and so Windows 7 users stood a better chance of getting something done compared to those same users moving to Windows 8.

After a few years of screaming outrage, Microsoft has fixed most of that in Windows 10. A Windows 7 user will not be lost in Windows 10 -- at least mostly. There's a Start menu, it's clear how to launch applications, and while the UI looks a bit different, it's now usable by traditional, experienced Windows users.

As a result, the Microsoft disadvantage has pretty much gone away. Yes, settings are different and a little less clear, but nothing a good Windows user can't handle. And sure, there are windowed applications and full-screen Metro-style apps, but it's now clear how to get in and out of those apps.

Decision: Microsoft. If you use Windows 7, you won't find Windows 10 foreign. By contrast, if you move to Mac OS X, the Finder is weird, you can't right-click to create a new file, and there are no running app previews unless you buy some add-on software.

Application selection

There are still more Windows applications than Mac applications. That said, because you can run Windows in a virtual machine on a Mac, but you can't run OS X in a virtual machine on Windows (at least without a Hackintosh hack), you can run a wider variety of software on the Mac.

That's precisely why I moved my main machines from Windows to Mac. I actively use a lot of Mac software as well as Windows software, and with Parallels, I can easily use both side-by-side on the same machine.

The big standard applications work well on both platforms. Microsoft's Office applications have been updated on the Mac and they're pretty much at parity with the Windows version. I now generally use the Mac version of Office with little difficulty -- although some of my 2,000-slide files crash on the Mac side, but open perfectly in the Windows VM.

Other standard applications, ranging from Adobe's Creative Cloud to Dropbox and Evernote to Chrome are virtually identical on both machines, so there's very little adjustment.

Decision: Mac, but only if you need to run both Mac and Windows applications. Otherwise, both platforms have a wide selection of applications with a deep history of solid support.


I've started thinking a lot about Windows reliability because Microsoft has been screwing with my previously rock-solid Windows 7 environments. But that's mostly because Redmond is obsessively pitching people to move to Windows 10.

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By most reports, Windows 10 is reasonably solid, at least on good hardware with good support. Because Windows 10 runs on a huge variety of hardware, you're going to see some systems that are more reliable and some that are less. But that's the nature of the huge Windows hardware ecosystem not Windows 10 itself.

On the Mac side, my experience with OS X was excellent -- except when it wasn't. When Apple rolled out the latest El Capitan update, they broke a few key features on my machine. An update to the update rolled out a month later, and now everything is back to normal. But there was a month of profanity, worry, and wasted time testing and diagnosing a problem that wasn't mine.

Decision: Draw. You need to take care to read reviews of the Windows 10 device you're buying, because they're not identical, but Windows 10 itself isn't any more or less solid than OS X.

Mobile ecosystem compatibility

Let's face it. Everything works with iOS. Given how huge the Apple mobile market is, no vendor can afford to ignore it. Microsoft is even known for releasing their own products on iOS before their Windows mobile offerings. Android, too, has strong support in both the Windows and OS X environments.

There are some factors, though. If you stay all Windows, all the way down to your phone, Microsoft has some excellent compatibility features, including the ability to dock your phone and get a traditional Windows desktop UI.

Likewise, if you're all Apple, you get the ability to smoothly use your iOS devices with your Mac in a nearly seamless way.

Android doesn't have quite as seamless an integration with either desktop environment, but there's also no clear desktop winner for Android users.

Decision: Mac. If you use Windows phones, you're a very small minority. By contrast, so many people use iPhones that the iPhone's smooth integration with OS X is a clear advantage -- but only if you're an iPhone user. If you happen to be one of those few Windows phone users, then Windows will clearly provide you with an advantage.


There will always be more security risks on Windows than on the Mac, simply because of Windows' market share advantage. Windows, as they say, is a target-rich environment. That said, Microsoft has done wonders with system security since the days of Windows XP, and even the days of Windows 7. Windows 10 is a much more secure OS than Windows 7,

There are fewer exploits and hacks into Macs, but that doesn't mean the Mac is perfectly safe. Most Mac users can get away without using an antivirus program, while Windows users would be suicidal to do so. But the Mac has seen its share of exploits and it can't be considered bulletproof.

Decision: Mac. There are simply less security hassles on the Mac side, although Windows has gotten much better.

Upgrade cost

Apple recently enacted a policy of free OS upgrades. Period. You won't have to pay for an upgrade when the new OS comes out.

By contrast, Microsoft has made Windows 10 upgrades free, but only for the first year after release. After that point, Microsoft says you'll have to pay to upgrade, which will likely run you from about $20 to over $200 per machine. That can add up quickly.

Decision: Mac. Granted, Apple makes most of its money from hardware and Microsoft has historically been a software only company, you won't ever have the question of how much you'll have to pay to upgrade your OS when you're using Apple products. Not so with Microsoft products.

Licensing and switching costs

We talked about the fact that high-quality PCs are as expensive as Macs, and we talked about the cost of upgrades. But what we haven't talked about is licensing or switching costs, which fall into two categories: your existing licensing agreements, and the cost of applications on a new OS.

If you have existing licensing agreements or contracts, you may or may not pay by the seat vs. the platform. For example, both Adobe and Microsoft charge by the seat. Microsoft doesn't care which platforms you use Office 365 on, just that you keep it inside your seat limit. Same with Adobe and Creative Cloud. I have one Mac and one PC on my 2-license Creative Cloud account and it works just fine (other than I think two licenses is unnecessarily stingy on Adobe's part).

But some license agreements may stipulate platform. If so, you may find switching to the Mac considerably more expensive.

This also applies to software where you don't have existing agreements. When I moved to the Mac, I bought a whole pile of new software -- mostly utilities -- and while not terribly expensive, it did add to my switching costs noticeably

Decision: Windows. You may run into extra licensing or switching costs when moving to the Mac.

Configuration variety

When it comes to the actual devices, Apple offers some options. You can purchase one of four laptop form factors (ranging from the MacBook Air to the 15-inch MacBook Pro), the cylindrical Mac Pro, the all-in-one iMac, and the little Mac mini.

But Windows... oh, boy. You can do laptops or you can do tablets or you can do detachable laptops that turn into tablets. You can do tower PC or you can do HDMI stick. There are an almost uncountable number of configuration varieties out there for Windows users looking for solutions.

But all magic comes with a price, and the price of the variety in Windows machines is there is also quite a range in reliability and driver quality. Some machines are going to be rock solid and others, well, not so much. Choosing a solid machine involves more than reading specs, you will often need to rely on reviews by other users and IT professionals to get a feel for what sorts of problems you may encounter down the line.

Decision: Windows by a mile, but with a caution: you takes your chances with some machines.

Stylus and touch

This one is a no brainer. While the iPad Pro with the Apple Pencil is reputed to be sublime, the Mac platform does not offer touch or a stylus. So if you want to use Photoshop with a stylus, you're either going to have to step off the Mac ecosystem or go with a Windows 10 machine.

Decision: Windows. Unlike Macs, nearly all Windows machines are touch-capable.


Gaming has gotten better on Macs and, without a doubt the gaming market for iOS devices is huge. But let's be clear here -- when you're considering Macs vs. Windows machines, you're probably not looking towards iOS. So don't confuse what you can do on an iPad with what you can do on a Mac.

Mac gaming, while not bad on some machines, is still nothing like PC gaming. When you're looking for the ultimate gaming experience, you're going PC. There's just no question about it.

There are some challenges, though. While Windows has better gaming support from the game vendors, and much better joystick and gamepad support if you're into such things, some PCs with graphics cards support very odd configurations and drivers.

My last Windows machine was a high-end gaming laptop which came with both an ATI graphics processor and a regular Intel video processor (for non-3D applications). The drivers on that machine were just never quite right -- and, in fact, the reason I'm not upgrading that machine to Windows 10 is the vendor says any attempted upgrade would just nuke the machine. The drivers just can't handle the upgrade.

Decision: Windows, but with the now-usual caveat that your mileage may vary.


As discussed earlier, the new Windows 10 UI won't be nearly as jarring to your Windows 7 users as the Windows 8 UI was.

As a result, most basic users won't need too much training to make the jump to Windows 10, where they might need more training to get used to OS X.

At the admin level, that's a bit different. Each operating system revision has its own quirks, and Microsoft has fiddled with settings and configuration options, so Windows 10 will take some getting used to. But if you make use of the search (and of the Google), you should be fine.

Decision: Windows. Moving to OS X will require more of a training load for your users than moving to Windows 10. For admins, both will have annoying behaviors and changes, but there's nothing that some good old-fashioned search engine jujitsu can't solve.

Directory integration

If your shop is using Active Directory, you are not limited to Windows only. There are quite a few add-on Active Directory products that fully enroll Macs into an AD environment. That said, native AD is native AD, and you won't have to incur licensing costs with Windows devices.

Decision: Windows. It's possible with Macs, but it will add to your costs.

The bottom line

We've looked at a lot of factors and attempted to answer the question, "If you're a Windows 7 user getting a new machine, should you upgrade to Windows 10... or move to a Mac?" While there are many nuances to that decision, here is a decision tree to take to management:

  • If you're worried about cost, there are certainly cheaper Windows devices, but quality PCs and quality Macs cost about the same. So that's a draw.
  • If you're very heavily invested in the iOS ecosystem, integration with Macs might justify moving to the Mac. Likewise, if you're one of the few organizations using Windows phone devices, then the mobile integration justifies staying on the Windows side.
  • If, like me, you need to run both PC and Mac applications, then a well-configured Mac is the best choice (and definitely beats having two machines, especially since you can cut and paste between OS X and a VM running Windows).
  • If you want a wide variety of form factors, then Windows is clearly your choice.
  • If you want a detachable screen, touch, or a stylus (and you're not going the iPad Pro route), then Windows is your choice.
  • If you want top-notch gaming performance, compatibility, and availability, Windows is your choice.
  • If your primary concern is security, Macs might be a better choice, but not definitively. Macs are normally left open and vulnerable because they don't run anti-malware software. On the other hand, they tend to be hit a lot less than Windows machines.
  • If you're concerned about reliability and system performance, then you'll do fine on both environments, but pick carefully and read reviews and buyer comments before buying a Windows machine. Quality varies far more among machines on the Windows side than those sold by Apple.

The real bottom line is this: you're fine staying with Windows, but the Mac is also a viable option. Microsoft has done a much better job with Windows 10 than with Windows 8 and so if you're buying a new machine, choose based on what you need. Neither OS is vastly better or worse than the other.

By the way, I'm doing more updates on Twitter and Facebook than ever before. Be sure to follow me on Twitter at @DavidGewirtz and on Facebook at Facebook.com/DavidGewirtz.

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