How to decide: Should you upgrade to Windows 10?

Buying a new PC -- or building one? Upgrading from Windows 8.1 or an earlier OS? David Gewirtz walks you through all the possibilities, so you're armed with the best decision-making strategy for your needs.
Written by David Gewirtz, Senior Contributing Editor

Updated: added note about Windows Media Center.

Upgrading an operating system is always a challenging decision, especially when it's a major upgrade, like Windows 10. After the even-worse-than-Vista debacle that was Windows 8, many die-hard Windows users are loathe to move off of trusted versions of their daily-driver OS. For Microsoft, though, Windows 10 is a make-or-break proposition. If they can't get users to upgrade, they will likely cede OS dominance permanently to Android.

In this article, though, we're not concerned about Microsoft's strategic needs. In this article, it's all about you. I'll walk you through a decision tree that will help you make the right decision.

If you don't have time to read all the details, you can skip to the end of the article and read a short summary of my recommendations. Before I get started, I should make one thing perfectly clear: we're talking about upgrading the traditional desktop version of Windows. Once you start talking Windows 10, you're talking about a wide variety of platforms, ranging for Raspberry Pi and up. In this article, we're going old school and talking traditional desktop OS.

Before (about) July 29, 2016

If you are running Windows 7 SP1 or Windows 8.1 (I'll come back to this in a moment), you can update to Windows 10 for free for what Microsoft calls "one year from the time Windows 10 is available," which should be just about July 29, 2016. After a year, you'll be paying about $119 for an upgrade. Why "about $119"? As with all things Microsoft, the company has a wide range of editions. Windows 10 has four Intel processor versions and two Arm-based versions.

Thankfully, our Ed Bott dug into the oddness that is Microsoft product management and has a good summary of each edition. For most of our discussion, we'll be discussing Windows 10 Home and Windows 10 Professional. Windows 10 Home is the base edition of Windows without such features as BitLocker, Hyper-V, Remote Desktop hosting, the ability to join Active Directory, and other business-oriented features.

Now, here's where it gets interesting. If you want the free upgrade, you're not getting a choice of editions. If you're running Windows 7 Home Premium or Windows 8.1, you're getting Windows 10 Home. If you're running Windows 7 Professional or Ultimate or Windows 8.1 Pro, you're getting Windows 10 Pro. One thing to keep in mind is that Windows 10 Home will have mandatory updates. While that's a great safety net for the many users who don't bother to update their machines, there's always the chance Microsoft will try to foist a toolbar or some other silliness as part of an "update."

In any case, do keep in mind that an upgrade will be far more cost effective if you do it before the one-year clock runs out.

If you're buying a new PC

Let's discuss the elephant in the room: Windows 8 (and, by extension Windows 8.1). Windows 8 is Dead OS Walking. Although there are some stats that say Vista was worse, the reality is Windows 8 is the version of the OS that effectively lost Microsoft the operating system wars.

While there could be no guarantee that if Windows 8 didn't suck so much, it would have beaten back the rush to Android and iOS, there's no doubt that the nearly insane product management decisions that went into Windows 8 turned the tables against Microsoft.

My point is that Microsoft and vendors are going to run as fast as their feet can take them from Windows 8. If they could, they'd erase history and never acknowledge Windows 8 existed.

And all that means is that if you're buying a new Windows PC, you're going to want to get a Windows 10 PC.

What about buying a Windows 8 or Windows 8.1 PC and looking for bargains?

This is a strategy, but be careful. First. if you went back and bought a Windows 8 PC, you'd first have to run an update to Windows 8.1, and then to Windows 10. Yes, the updates are free, but by that time, you'll have a pretty crufted install and, more to the point, you might have some compatibility problems because this late in the game, there really shouldn't be any Windows 8 PCs floating around the channel.

If you're able to get a relatively recent Windows 8.1 machine as a deal and then update it to Windows 10, that's not a bad idea. Just keep in mind that you may run into compatibility issues because the manufacturers are unlikely to be maintaining Windows 8 or Windows 8.1 machines and their drivers with anything resembling love. So it's likely your machine may orphan quite a lot faster than if you were to spend the extra few bucks and buy a new Windows 10 PC.

If I were buying a new PC, I'd go straight for Windows 10.

What about buying a PC with Windows 7?

For you folks in the enterprise world, Windows 7 is still available on new PCs. Whether you go this route really depends on what software and systems your organizations are running. Because Windows 7 is now six years old, you're also likely to run into compatibility issues with new devices and drivers.

Here's how I'd make this decision: if you're an individual buying a new PC, get Windows 10. If you're in an enterprise, that should be a decision best left up to your corporate IT team. If you are the corporate IT team, you should know the trade-offs and make your decision accordingly.

If you're building a new PC

I'm going to introduce here a theme you'll read over and over in this article: drivers are the issue. While some most vendors are likely to maintain their Windows 7 drivers for a long time (it's the majority of the market, after all), new hardware will begin to move off of Windows 7 relatively soon - especially gaming hardware.

If you're going to build a new Windows PC now, I'd make it Windows 10.

If you're running Windows RT

Let's get another bit of weirdness out of the way. When I'm talking Windows 8, I'm talking Intel Windows 8, not that oddity called Windows RT. If you were one of the unfortunates who bought a Windows RT machine, then there is a chance Microsoft will issue an upgrade. Maybe.

If Microsoft does, then I'd recommend you jump on the upgrade. Windows 10 is designed to work all across the size spectrum and while the ARM processor in RT machines won't let you run most desktop apps, you'd be able to turn your Windows RT boat anchor into a glorified tablet and maybe get some service out of the thing. Just triple-check Microsoft compatibility statements, because there are very few system level tools out there for recovering from a failed RT upgrade.

Heck, at the price of new Windows machines, just toss the RT machine in the trash and buy a new PC.

If you're running (real) Windows 8 or Windows 8.1 on a traditional PC

If you're running Windows 8 and you can, you should update to 8.1 anyway. And if you're running Windows 8.1 and your machine can handle it (check the compatibility guidelines), I'd recommend updating to Windows 10. In terms of third-party support, Windows 8 and 8.1 will be such a ghost town that it's well worth doing the upgrade, and doing so while the Windows 10 option is free.

That said, if your users have already gone through a painful adjustment to the Windows 8 user experience, Windows 10 will involve another adjustment. Fortunately, nearly everyone is familiar with the old Start menu interface, and Windows 10 supports it, albeit with a bit of Metro slapped on the side. Even so, very few Windows 7 and prior users will be as lost on Windows 10 as on Windows 8.

If you're running Windows 8 or Windows 8.1 on a tablet

The big question is whether you'll have enough space. Microsoft says the Windows 10 upgrade requires 16 GB for 32-bit OS 20 GB for 64-bit OS, so you'll have to make that determination before you try to upgrade.

What would I do? Frankly, tablets are pretty self-contained environments and if you like your Windows 8 tablet as is, I wouldn't rush to upgrade. There's no guarantee that the new version won't drag down performance on the machine you're using. I upgraded my trusty original-edition Nexus 7 from Android KitKat to Android Lollipop, and performance cratered. That happy little device was never the same.

Yes, there are improvements in Windows 10, but keep in mind how you use your tablet and make your decision accordingly.

If you're using Windows Media Center

Those of you who are still using Windows Media Center will want to watch out. Upgrading to Windows 10 will remove WMC functionality. That said, I use the old XBMC, now known as Kodi, and I like it a lot.

If you're running Windows 7

I'll tell you this: I am not going to update any of my Windows 7 machines. No way. They work, they're rock solid, and all their drivers are perfectly tuned to the hardware they're running on. I'm leaving well enough alone.

As for you, you'll need to decide if you want any of the features of Windows 10 so much that you want to upgrade. If you have an Xbox One and want to stream games to your PC, then you'll want Windows 10. If you want to try out HoloLens or Oculus Rift, you'll want Windows 10. If your organization is all-in on Microsoft products from phones through tablets up through desktop PCs, then you'll probably want Windows 10.

But if you're a regular ol' PC user and you like Windows 7 on your current machine, stay with it. It works. Move to Windows 10 when you get a new machine.

If you're still running Windows XP

Face it, the curtain is closing on Windows XP. If you're still running Windows XP, it's either because you never wanted to move off of it, your machine isn't compatible with newer versions, you've been living under a rock, or you just don't care.

The fact is, you're unlikely to be able to make the move to Windows 10 (at least for most old XP machines). That said, Windows 8 and 8.1 run quite nicely on older machines.

At this point, I wouldn't necessarily advise you to go out and buy Windows upgrades for those XP machines, but if you happen to have Windows 8 licenses running around, it wouldn't hurt to move whatever you can to a later (and far more secure) OS. That said, it's really probably time your XP boxes join Windows RT machines on the scrap heap of history. Certainly, never, ever connect to the Internet with an XP machine.

If you're running Windows Vista

Wow, I almost forgot to even mention Windows Vista. If you're still running Windows Vista, like with XP, you probably have your reasons. I do recommend you move on, but you probably won't listen. Sadly, you can't upgrade to Windows 10, but you could move to Windows 8.

From Windows 8, you could update to Windows 8.1 and from Windows 8.1 you might be able to go to Windows 10. Will you? If you never upgraded to Windows 7, the odds are you're not going to jump through the big hoops needed to get to the big 1-0.

Recommendation summary

The following set of recommendations are weighted by the assumption that you're updating (or considering updating) before Windows 10 stops being a free update. That said, most of the following choices are still relevant, just factor in the cost component if you're reading this sometime in the future.

  • If you're buying a new PC: Go ahead and get it with Windows 10. Windows 8 and 8.1 machines are about to become ghosts.
  • If you're buying a Windows 8 or 8.1 PC and looking for bargains: Probably too much work to buy an 8 or 8.1 machine and upgrade to Windows 10. There might be driver and compatibility issues. That said, if you want to be frugal and can live with the probable pain, go for it.
  • If you're buying a PC with Windows 7: If you're buying a Windows 7 machine now, it's because you want Windows 7.
  • If you're building a new PC: You'll want Windows 10, especially if you want to do cool things with games and VR.
  • If you're running Windows RT: Toss it in the trash and buy yourself a useful machine. There might be a chance you can upgrade to Windows 10, but you'll probably run into storage and other hassles.
  • If you're running real Windows 8 or 8.1 on a traditional PC: Upgrade right away. Windows 8 and 8.1 are about become forgotten to history.
  • If you're running Windows 8 or 8.1 on a tablet: Probably best to stick with 8.1. If you're running Windows 8, move to 8.1. Windows 10 might work, but it might not be worth the risk.
  • If you're running Windows 7: Unless you absolutely love one of the Windows 10 new features (most notably Cortana or the gaming features), you should stick with Windows 7. I'm not upgrading my Windows 7 machines.
  • If you rely on Windows Media Center: Windows 10 will remove it.
  • If you're running Vista: Find thee a dumpster.
  • If you're running XP: Look, you know who you are and why you're still running XP. You should stop, but you're not going to, are you?

There you go. Don't forget to visit ZDNet's comprehensive Windows 10 topic section for all the latest in Windows 10 news. And remember, Windows upgrades go best with pizza and the non-alcoholic beverage of your choice. Don't drink and install drivers.

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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