Windows 10 is coming - what will it take for you to upgrade?

We now know that the free upgrade offer that arrives with the operating system will allow for clean OS installs, that it won’t be locked to a previous version of Windows 7 or 8.1, and that users won’t have to keep an image of an old OS handy in case they ever want to reinstall. There are still questions about other aspects of the license, but this major point has been resolved. We also know that the OS is going to pioneer a Windows-as-a-service model, offer some interesting Xbox Live cross-play opportunities, and, of course, features like DirectX 12.

The one thing we don’t know — and by “we”, I mean both tech journalists, users, and Microsoft itself — is whether or not the mass of people still using Windows XP, 7, and 8/8.1 will actually upgrade. According to the OS data available at NetMarketShare, Windows 7’s total market share has actually increased over the past 12 months, up 6% while Windows XP marketshare fell a bit over 10%. Windows 8.1 and Windows 8 together barely account for 16% of the market. By any measure, that’s a terrible result for a version of the Windows operating system that turns three this year.

Interestingly enough, Steam’s data cuts sharply in the other direction. While Windows 7 64-bit remains the most popular OS overall, at 46.76%, Windows 8.1 64-bit is firmly in second place, at 30.15%. This suggests that there’s a core of gamers who have updated more recently, with fairly good uptake of Windows 8/8.1 — double the average share in the overall market.

So, the big question for the day is, will you upgrade or not — and if you’re on the fence, what are you waiting to find out before you decide?

Personally, I’m hoping that Windows 10 is an OS I can upgrade to. I skipped Windows 8/8.1, not because I thought the Desktop side of the equation was bad, but because I thought Metro was such an abysmal trainwreck. Paying for Windows 8 felt like telling Microsoft “I’m ok with the condition of the operating system you shipped.” I fundamentally wasn’t. Windows 8.1 improved the OS in a number of ways, but the Windows Store is still abysmally curated, the “Metro” applications still struggle to replicate basic functionality that their Desktop counterparts have had for years, and the app-pinning and switching behaviors were difficult to utilize if you’ve been trained to alt-tab between windows for the past 25 years. Without a way to save groups of Windows and switch between sets of pinned applications, a quick Alt-Tab could easily force the end-user to laboriously re-pin applications.

The Start Screen may have drawn heavy fire from end-users who hated the look and feel of the OS, but that wasn’t what killed it for me. The inability to change file organizations or layouts in Metro apps, the trumpeting of resizable Windows as a major feature addition (shades of Windows 2.0 in that announcement) — all of these elements combined left me unwilling to pay Microsoft for an operating system I knew I’d have to custom-revert back into an older mode of operation just to put up with it. I’d have taken Windows 8 if I’d bought a new system that came with it, but paying retail for a copy? No thank you.

So far, Windows 10 looks like it fixes most of what I disliked about Windows 8, includes the performance features that I liked about Windows 8 from the beginning, adds new capabilities like DX12, and extends the OS in a more sane manner. After the trainwreck of Windows 8 I’ll admit to being cautious, but I’m hoping this is an upgrade I can say yes to.
What about you? What will it take to get you onboard the Windows 10 Upgrade Train?