It's really no different than Apple in my view. Apple pushes updates to OSX pretty heavily, even when they are major revamps.
The only reason I think people are hesitant to upgrade, was due to the nature of upgrades in previous versions of Windows. Upgrading to a new version of Windows was overall fairly risky, 10% of upgrade installations have failed or had some major quirk in my experience.
So far though, every single Windows 10 upgrade has worked nearly flawlessly. I did have one install bluescreen on its first startup, but that could have merely been a coincidence or a driver issue. It's about time Microsoft got upgrading right.
Well to be fair, most of the OS-level upgrades that people tend to experience pain with, is when they are moving between major Kernel versions.
Every NT 6.x upgrade for me has been flawless. I went from Windows 7 to 8 and then 8.1. I would have went to Windows 10 but over the years I had built up numerous drivers and configurations and it was resulting in various odd issues here and there, so I started with a clean 8.1 installation and then upgraded to 10. Very smooth experience.
I reckon going from Windows 7 to 10 should be relatively painless, but due to the number of years between those two releases, there will be the occasional driver issue. For many home users, this will present as a "bad upgrade, don't do it!", but for most of us, it's a stupidly simple troubleshooting process. Well, it can be, depending on how many drivers and what kinds of conflicts or incompatibilities actually exist. I could have continued fixing my system, but it was becoming a laborious process. It takes a long time for those kinds of issues to finally make me give in, considering there were many deep conflicts, and especially considering I loathe starting over. So much to reinstall and reconfigure. Ugh.
I really should make an image one of these days for my main system...
For light users who have recent peripherals and didn't use their XP-era hardware, a Windows 7 > Windows 10 upgrade path should be smooth. Windows 10 is NT v10, but frankly, it's basically v6.4 for all intents and purposes.
As long as the kernel stack stays relatively consistent from here on out (of which it has, for the most part, since 6.0 aka Vista), I think Windows 10/NT 10 should be a wonderful future upgrade path. With new versions for the foreseeable future likely keeping to the NT 10.x family, a point release here or there will likely be more akin to a Service Pack than a brand new OS. Much more in line with OS X upgrades in their 10.x family - small feature additions here and there, baked into a smooth in-place update package rather than a full-blown OS overhaul. Microsoft could have accomplished that at any time, but they wanted to keep the old revenue model. But now, with the unified platform fully prepped, they are in the correct position to make that change and keep revenue flowing.
They've previously shown they could introduce major changes in the form of a Service Pack, and increment the NT version in the same OS core at the same time. That had did that with XP. I think Windows 7 was just a quick way to distance themselves from Vista because the kernel hardly changed. Vista was just fine but the radically different kernel stack in NT 6.0 caused a lot of issues with driver makers after having come NT 5.x drivers.
They essentially did the same with Windows 8/8.1 as they did in Windows XP, and theoretically could have made 10 v8.2 instead, but it did make far more sense to start over to distance it from the 8.x family, and also because the the GUI was much different and now the true Universal Windows Platform is basically feature complete from the integration aspect.
I think they can clean up how they do the updates now in Windows 10, but they are certainly on the right path when it comes to helping keep systems secure. Unfortunately, the hardware configuration possibilities in Windows systems is a ridiculous complication, so some updates will cause instability or break something - an issue rarely encountered by Apple (comparatively speaking).