Things like Cortana are like the fabled frog in a pot of boiling water. As long as you change slowly enough, people adapt. Someone above mentioned XP activation. I remember that debacle. And now, nobody cares at all. It's just a given. Or how about the Pentium 3 unique serial number thing? People are quick to anger, and just as quick to forget. You just have to survive the initial outrage and let it blow over and become normalized. In ten years, our insurance company will be well aware of how many often we go out to eat, or drink beer with buddies, and it will just be the way it is. Given human nature, and especially capitalist motivation, that's kind of terrifying.
As far as the future of software, there are only really a handful of models, currently, that are known to work:
1) Free, as in open source. Linux, BSD, etc. Doesn't cost anything but time and effort, but it's not necessarily a well-organized project with clear goals and aims. Will probably never be the primary model - at least not without a secondary revenue stream.
2) Advertising-driven, as in Google. Leads to the inevitable outcome of "private" information being bought, sold, and shared between various organizations. Things change on a whim, and you've got no say. (Remember Bump? Or Google+?) We're at a point now where the public is just starting to understand the real cost of this model. I doubt it will matter in the long run. Free (or, no $$ anyway) is king.
3) The Apple model -- i.e., integration. I think this is what Microsoft was trying to do, but they're too naive to understand that OS X works as a series of point-releases, for free (or in the past, at a trivial cost), because of the mandatory hardware sales. From an accounting and user point of view, the OS is just the software what makes the computer work. Not a product unto itself. It doesn't have to be profitable. (But of course it is -- it's the reason to buy a MBP or an iPhone, for most people.) Apple has a case of the dumb right now, but they've been down many times before. Don't count them out yet.
4) Retail (to include volume licensing as a CapEx purchase.) This implies the product stays a discrete product. You're buying something tangible. Updates require some incentive, otherwise the customer base just keeps using the one they have perpetually. (Or, you get the silly "OEM" licensing stipulation... "You can only use this on this one computer, ever, then you have to stop and buy a new license. Promise?")
5) Subscription. The "as a service" model. You pay for the product on a schedule. Like anti-virus, or web hosting, or O365. Rolling updates, no guarantee of entitlement, and typically some automated form of enforcement that requires regular or constant connectivity. The product exists as long as there's a way to activate it. For those of us that are collectors and preservationists, it's the worst possible option.
I don't know how Microsoft intends to turn Windows into Mac OS. The industry, in general, has given the Surface line a resounding... "meh." All the IT geeks (a group to which I belong) and pointy-haired managers love them, because it's so futuristic to scroll and move windows by dragging your meaty paws all over a nice glossy screen, but touch is not going to be the way forward for productivity UI. Just ask Windows 8. And without touch, the Surface is just an expensive, buggy, poorly-designed laptop. So without the hardware lust of the Apple fan club, and without big, important-sounding updates to the OS as a tangible product (where, in the past, they mostly just re-organize the control panel, hide all your settings behind three layers of dialogs, and add a new skin), how is this going to work in the retail channel again?
In the enterprise sector, VL is often already consumed as a kind of a subscription model. Many (most?) just go the Software Assurance route and toss it on the OpEx pile. Many (most?) consumers just get a new version of Windows when they buy a new computer every few years. So what do you do with everybody else? If I buy Windows 10 Retail, do I get a lifetime of updates for free? THAT's clearly not going to work. So which way is it going to go? Ad-supported, or subscription?