I sat down in my office this morning and found a new icon in the system tray notification area of my Windows 7 Enterprise desktop. Right-clicking it showed four options, none of which was “Exit.” Left-clicking it brought up this window…

I’m not sure when Microsoft installed this program, but it must have been last week when the Tuesday update batch hit. None of the actions in the window appealed to me this morning. I don’t know what it means to “reserve” my free upgrade, and I am still not sold on Windows 10. Since I couldn’t get rid of the program (at least not without hunting down the process and killing it, after which it would in all likelihood return on the next restart) I used the notifications manager to hide it.

It’s not that I’m uninterested in Windows 10. On the contrary I’ve been very interested in all of Microsoft’s most recent decisions with their ecosystem, including the move to open source .NET and make the CLR portable across systems. And the truth is that I was a Microsoft platform developer for twenty years. It’s safe to say I have never before been two whole versions behind the current release of the operating system. Why, then, am I still running Windows 7? Should I upgrade to Windows 10?

I’m still running Windows 7 because Windows 8 sucked hard, in my opinion. I installed it. I used it. My wife has it on her laptop and I tried to help her a bit during the acclimation phase, and I thought it was horrible. I’m a software developer and the interface of Windows 8 did nothing other than make everything I already knew how to do cumbersome and difficult, with no compensating benefit that I could detect. I don’t have two 24″ monitors so I can cover them with big tiles.

I felt pretty much the same way about Windows Vista, but for different and more technical reasons. Windows Vista just wasn’t ready. Windows 8 just didn’t make any sense, ready or not. However Windows Vista became Windows 7, easily the best version of the OS that I have used, and a pretty high bar which Windows 8 certainly did not manage to leap over, at least in my view. Now that Windows 8 is becoming Windows 10 is it time to switch?

Even without thinking too deeply about it I’m biased against. The main reason is the deprecation of Windows Media Center. Microsoft is giving up on the desktop entertainment functions of the PC, apparently. But for me WMC has long been my Netflix solution of choice. It looks and works great and my ten year-old Firefly RF remote works awesomely with it. I realize, unfortunately, that this technology is aging, so maybe I should just get over it. What else does Windows 10 offer me, other than correcting the things people saw as mistakes in Windows 8? Let’s have a look at their news release. What are the big features a professional developer like me should care about?

Cortana, the world’s first truly personal digital assistant helps you get things done. Cortana learns your preferences to provide relevant recommendations, fast access to information, and important reminders. Interaction is natural and easy via talking or typing. And the Cortana experience works not just on your PC, but can notify and help you on your smartphone too.

Awesome, a digital assistant. I don’t really need one on my desktop. It might be useful in a mobile context, but I don’t run Windows Phone and I am not likely to anytime soon. Then again my kids all have iPhones with Siri, and I don’t hear them talking to their phones. As far as I know they don’t use Siri for anything. Maybe if I went to San Jose I’d encounter lots of people asking their phones to do things, but I just don’t see it happening around here, at least not in public.

Microsoft Edge, is an all-new browser designed to get things done online in new ways, with built-in commenting on the web – via typing or inking — sharing comments, and a reading view that makes reading web sites much faster and easier. With Cortana integrated, Microsoft Edge offers quick results and content based on your interests and preferences. Fast, streamlined and personal, you can focus on just the content that matters to you and actively engage with the web.

Well, web apps are still a big part of what I do so I will be getting familiar with Edge whether I want to or not. Am I excited about getting Windows 10 so Edge can replace my current browser? Let’s see… it has Cortana integrated… w00t. See above. And a new “reading view!” I’ll be keeping an eye on Edge in terms of standards compliance and performance, of course, and I will be testing web apps on it, but if those are the big draw features I’ll continue to bounce back and forth between Chrome and Firefox as one or the other alternately pisses me off.

Office on Windows: In addition to the Office 2016 full featured desktop suite, Windows 10 users will be able to experience new universal Windows applications for Word, Excel, and PowerPoint, all available separately. These offer a consistent, touch-first experience across a range of devices to increase you productivity …

I’m not even going to bother with that whole quote. I love Windows, but if there was ever a good reason to hate Windows it would have to be related to Office somehow. From a word processor so horribly complicated that no living human can enumerate more than 10% of the feature set to an email cum personal productivity tool that set a new standard for how long a legacy code base can continue to be crammed into ever more ill-fitting skin, there is literally nothing about Office that I like. Been using Google Docs for years and the words “touch-first experience” in the quote above certainly don’t give me any reason to rethink that choice. Yuck.

Xbox Live and the integrated Xbox App bring new game experiences to Windows 10. Xbox on Windows 10 brings the expansive Xbox Live gaming network to both Windows 10 PCs and tablets. Communicate with your friends on Windows 10 PCs and Xbox One – while playing any PC game.

Ok, that’s fine. I’m not a console gamer, and I don’t own an XBox, but this is still pretty cool and if I were a console gamer, or was willing to purchase an XBox to replace Windows Media Center, this might be exciting.

New Photos, Videos, Music, Maps, People, Mail & Calendar apps have updated designs that look and feel familiar from app to app and device to device.  You can start something on one device and continue it on another since your content is stored on and synched through OneDrive.

Wow, now this is what I was waiting for. Not. There are better services available now for all this stuff. Definitely will be meaningful to the thousands of people on Windows Phone, though. Next.

Windows Continuum enables today’s best laptops and 2-in-1 devices to elegantly transform from one form factor to the other, enabling smooth transitions of your tablet into a PC, and back. And new Windows phones with Continuum can be connected to a monitor, mouse and physical keyboard to make your phone work like a PC.

I’m not writing this off. Device convergence has been talked about for a long time, and I certainly hope somebody is able to make it happen. The vision of being able to use one device across different inputs and display form factors is compelling. But the problem Microsoft has is they don’t have the dynamic mobile ecosystem to pull this off and make it relevant to lots of people. Jury is out, but give them credit for the attempt anyway.

Windows Hello, greets you by name and with a smile, letting you log in without a password and providing instant, more secure access to your Windows 10 devices. With Windows Hello, biometric authentication is easy with your face, iris, or finger, providing instant recognition.

Same thing. Not writing it off, despite the ridiculous name. Also not relevant to me sitting here at my desk. So like the Continuum feature it is interesting, but provides no motivation to move me off 7 for my work system.

Windows Store, with easy install and uninstall of trusted applications, supported by the broadest range of global payment methods.

When lots of people are running Windows on their phones this will be a very compelling offering. Which is just a bit like saying that when I win the Powerball I will be living in a beachfront home in Santa Barbara. I understand Microsoft’s dilemma, and I don’t envy them. They have to be relevant to mobile, even though they are barely relevant to mobile. You can’t build the future of your business on desktop computing, even though most of the people who use your current product use it at a desktop, for work.

It’s a tough situation, but the reality for me is that reading through this feature list doesn’t make me wonder whether I should upgrade to Windows 10 on my desktop: it makes me wonder why I am still running Windows on my desktop at all. I also have an Ubuntu development box and switching would be pretty painless for me. The answer is: games and Steam, and to a lesser extent a huge file called outlook.pst. I play games like Battlefield 4 and Planetside 2, and I like a mouse and keyboard for that. And I have ten years of history in my outlook file. I never look at it, but for some reason I haven’t been able to just delete it. If I ever get to that point and also stop playing shooters (which I should do since I basically just get slaughtered by teenagers) that will probably be it for Windows.

So the answer to the original question I posed to myself in the title appears to still be “no.” I’ll be giving Windows 10 a look in a VM at some point, and at some other point, hopefully still well into the future, I am going to be faced with the fact that I just can’t continue running Windows 7. I suspect that what will happen then is my Ubuntu and Windows machines will switch roles. Instead of having Windows drive my two monitors and using NX to access Ubuntu in a window it will be the other way around, and I will be switching into Windows every now and then just to play a game, or to actually try and find something in that huge Outlook file.